VANGUARD/WINDSOR FUNDS INC
N-30D, 1999-12-16
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VANGUARD
WINDSOR
FUND

Annual Report
October 31, 1999

[SHIP GRAPHIC]
[A MEMBER OF THE VANGUARD GROUP(R) LOGO]

<PAGE>

[PHOTO OF JOHN C. BOGLE]
JOHN C. BOGLE

FELLOW SHAREHOLDERS:

     TWO ROADS  DIVERGED IN A WOOD,  AND I--I TOOK THE ONE LESS TRAVELED BY, AND
     THAT HAS MADE ALL THE DIFFERENCE.

I can think of no better  words than those of Robert Frost to begin this special
letter to our shareholders,  who have placed such extraordinary  trust in me and
in Vanguard  over the past quarter  century.  When the firm was founded 25 years
ago,  we  deliberately  took a new road to  managing a mutual  fund  enterprise.
Instead of having the funds controlled by an outside management company with its
own  financial  interests,  the  Vanguard  funds--there  were  only  11 of  them
then--would be controlled by their own  shareholders and operate solely in their
financial interests.  The outcome of our unprecedented  decision was by no means
certain. We described it then as "The Vanguard Experiment."
     Well, I guess it's fair to say it's an experiment no more.  During the past
25 years,  the assets we hold in  stewardship  for investors  have grown from $1
billion  to more  than  $500  billion,  and I believe  that our  reputation  for
integrity,  fair-dealing,  and sound investment  principles is second to none in
this  industry.  Our  staggering  growth--which  I  never  sought--has  come  in
important part as a result of the simple investment ideas and basic human values
that are the foundation of my personal philosophy.  I have every confidence that
they  will  long  endure at  Vanguard,  for they are the  right  ideas and right
values, unshakable and eternal.
     While Emerson believed that "an institution is the lengthened shadow of one
man," Vanguard today is far greater than any  individual.  The Vanguard crew has
splendidly  implemented  and  enthusiastically  supported our founding ideas and
values, and deserves the credit for a vital role in forging our success over the
years.  It is a  dedicated  crew of fine human  beings,  working  together in an
organization  that is well prepared to press on regardless long after I am gone.
Creating and leading this  enterprise has been an exhilarating  run.  Through it
all,  I've taken the kudos and the blows  alike,  enjoying  every  moment to the
fullest,  and even getting a second chance at life with a heart transplant three
years ago. What more could a man ask?
     While I shall no longer be serving on the Vanguard  Board, I want to assure
you that I will remain  vigorous and active in a newly  created  Vanguard  unit,
researching the financial markets, writing, and speaking. I'll continue to focus
whatever  intellectual  power and  ethical  strength  I possess on my mission to
assure that mutual fund investors everywhere receive a fair shake. In the spirit
of Robert Frost:
     BUT I HAVE PROMISES TO KEEP,  AND MILES TO GO BEFORE I SLEEP,  AND MILES TO
GO BEFORE I SLEEP.
     You have given me your loyalty and friendship over these long years,  and I
deeply  appreciate  your  thousands  of letters of support.  For my part, I will
continue to keep an eagle eye on your  interests,  for you deserve no less.  May
God bless you all, always.

/S/
JCB

- --------------------------------------------------------------------------------
CONTENTS

REPORT FROM THE CHAIRMAN ............1    PERFORMANCE SUMMARY ................11

AFTER-TAX RETURNS REPORT ............5    FUND PROFILE .......................12

THE MARKETS IN PERSPECTIVE ..........6    FINANCIAL STATEMENTS ...............14

REPORTS FROM THE ADVISERS ...........8    REPORT OF INDEPENDENT ACCOUNTANTS ..23

- --------------------------------------------------------------------------------
<PAGE>

REPORT FROM THE CHAIRMAN

[PHOTO OF JOHN J. BRENNAN]
John J. Brennan

Vanguard  Windsor  Fund  posted a return of 13.7%  during the fiscal  year ended
October 31, 1999.  While this was a solid result that surpassed the 11.7% return
of the average comparable fund, it was well behind the outstanding 25.7% advance
of the Standard & Poor's 500 Index,  which was propelled by a roaring market for
large technology stocks.
     The table at right  presents  Windsor's  fiscal year total return  (capital
change  plus  reinvested  dividends).  It also  lists  returns  for the  average
multi-cap  value fund (the category in which fund analyst Lipper Inc. has placed
Windsor, which holds both large- and mid-capitalization  stocks), as well as for
the S&P 500 Index and its value-stock  component.  The fund's return is based on
an increase in net asset  value from  $16.34 per share on October 31,  1998,  to
$16.91 per share on October  31,  1999.  The return is  adjusted  for  dividends
totaling $0.24 per share paid from net investment  income and a distribution  of
$1.23 per share  paid in  December  1998 from net  realized  capital  gains.  We
estimate that the fund will make a distribution of approximately  $1.88 from net
realized capital gains in December 1999.

- ------------------------------------------------------------
                                             TOTAL RETURNS
                                           FISCAL YEAR ENDED
                                           OCTOBER 31, 1999
- ------------------------------------------------------------
Vanguard Windsor Fund                                  13.7%
- ------------------------------------------------------------
Average Multi-Cap Value Fund*                          11.7%
- ------------------------------------------------------------
S&P 500 Index                                          25.7%
- ------------------------------------------------------------
S&P 500/BARRA Value Index                              19.0%
- ------------------------------------------------------------
*Derived from data provided by Lipper Inc.

FINANCIAL MARKETS IN REVIEW
The fiscal year ended October 31 comprised two distinctly  different halves. For
most of the first half, stock prices  worldwide were rebounding  strongly from a
slump in the summer of 1998 that had been  prompted by economic  crises in Asia,
Russia,  and parts of Latin America.  The stock market's comeback was aided by a
pickup in global  economic  activity  and by  interest  rate  reductions  by the
Federal  Reserve  Board  that  autumn.  These  developments--and  the  continued
ebullience of the U.S. economy--erased investors' fears that the troubles abroad
would depress business  activity and profits at home. Even though interest rates
rose during the six months from October 31 through  April 30, the stock  market,
as measured by the Wilshire  5000 Total Market  Index,  gained 22.8% and the S&P
500 Index was up 22.3%.
     However,  during the  second  half of our fiscal  year,  most stock  prices
stagnated  or fell  (with the  notable  exception  of  technology  stocks).  The
Wilshire 5000 advanced  2.3%,  bringing its full-year  return to 25.7%.  The S&P
500's second-half return of 2.7% brought it to an identical 25.7% return for our
fiscal year.  Large-cap growth stocks were the strongest  market sector,  led by
simply  stupendous  gains for a number of dominant  technology  stocks,  such as
QUALCOMM (700%), Sun Microsystems (263%), Cisco Systems (135%), Microsoft (75%),
and Intel (74%).  The growth stocks  within the S&P 500 gained 31.6%,  while the
index's value stocks,  as measured by the S&P  500/BARRA  Value Index,  returned
19.0% as a group.  Small-cap stocks were left in the wake of the big stocks: the
Russell 2000 Index

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<PAGE>
of small stocks gained 14.9%.  The  growth/value  split was even wider among the
small-caps,  as the Russell 2000 growth stocks gained 29.3% versus a paltry 0.7%
return for the index's value stocks.
     One drag on the stock  market in general  was a strong  uptrend in interest
rates that began in February.  The Federal Reserve  encouraged this move, acting
in late June and again in August to boost  short-term  interest rates by a total
of 0.5 percentage  point.  Fears of a global  economic slump were  supplanted by
worries that economic  growth--  especially in the United  States--was so strong
that it would cause wages and commodity prices to surge, pushing up inflation.
     For  the  full  year,   yields  on  long-term  U.S.   Treasury  bonds  rose
significantly.  The yield on the 30-year Treasury increased exactly 1 percentage
point (100 basis points) to 6.16% on October 31, 1999.  Bond prices,  which move
in the opposite  direction from interest rates, fell during the year. The Lehman
Brothers  Aggregate Bond Index, a benchmark for taxable bonds, eked out a return
of 0.5% for the year,  as its interest  income of 6.2% only barely  offset price
declines of -5.7%.

FISCAL 1999 PERFORMANCE OVERVIEW
Windsor Fund's 13.7% return during the fiscal year was 2 percentage points ahead
of that of the average  multi-cap  value  fund--the  category  that  Lipper--and
Vanguard,  for that  matter--regards  as the  correct  peer group.  However,  we
trailed the S&P 500 Index's 25.7% return by 12 percentage points.
     Half of our performance gap versus the index can be explained by the simple
fact  that  during   fiscal   1999,   growth   stocks--whose   relatively   high
price/earnings,   price/book  value,  and  price/dividend  ratios  reflect  rosy
expectations  for future  growth--ruled  on Wall Street.  As noted earlier,  the
return for growth stocks within the S&P 500  outdistanced  that for value stocks
by nearly 13 percentage  points--31.6%  versus 19.0%.  Several large tech stocks
are selling at prices of $50 or more per $1 of earnings,  while large industrial
companies are selling for $10 to $20 per $1 of earnings.  Time will tell whether
the great expectations for growth built into tech stock prices will be justified
by actual earnings.
     Value  stocks--particularly  in such  sectors as  materials  &  processing,
producer durables, big oil companies, and utilities--enjoyed a powerful rally in
April and May,  outperforming  their growth stock  competitors by 9.8 percentage
points in those two months.  But the resurgence  was brief,  and the market soon
resumed its love affair with tech stocks.  Within the S&P 500, technology stocks
posted a 67% gain during our fiscal year.  Windsor Fund's tech holdings earned a
similar 66% return,  but our stake in this group averaged about 4% of assets,  a
fraction of the 18% weighting  for tech stocks in the S&P 500.  Given the fund's
value investing style and mandate to seek growth and income, it would be odd for
it to emphasize  technology stocks,  with their high valuations and low dividend
yields. (Only 19 of 52 tech stocks in the S&P 500 pay any dividend at all.)
     Another  reason  for  our  shortfall   versus  the  broad  index  was  poor
performance  of our  holdings  in several  sectors,  including  "other  energy,"
financial  services,  and health care.  We were hurt,  for  example,  by HMO and
hospital stocks that suffered due to pricing  pressures and concerns about legal
and  regulatory  difficulties.  One plus for your  fund was our  light  stake in
consumer-staples  companies such as beverage and food makers. We held an average
of just  0.5% of  assets  in  this  sector,  which  was  the  market's  weakest.
Interestingly,  our light  weighting in this sector  stemmed from the same value
disciplines that have kept us from investing heavily in technology.

                                       2
<PAGE>

     As you know,  during the year Sanford C.  Bernstein & Co. began  managing a
portion of the fund's assets,  joining our lead adviser,  Wellington  Management
Company.   The  transition  went  smoothly.   Careful   planning  and  excellent
cooperation  between  our  advisers  minimized  the  costs  associated  with the
movement of some $4 billion in assets to Bernstein & Co. We estimate  that these
one-time  transaction costs trimmed the fund's return by 0.10 to 0.20 percentage
point.
- ------------------------------------------------------------
                                        TOTAL ASSETS MANAGED
                                      AS OF OCTOBER 31, 1999
                                      ----------------------
                                       $ MILLION     PERCENT
- ------------------------------------------------------------
Wellington Management Company, LLP       $12,595         75%
Sanford C. Bernstein & Co., Inc.           4,080         24
Cash Reserve*                                149          1
- ------------------------------------------------------------
Total                                    $16,824        100%
- ------------------------------------------------------------
*    This  cash  reserve  is  invested  in  equity  index  futures  to  simulate
     investment in stocks; each adviser may also maintain a modest cash reserve.

     The table above shows the share of assets supervised by each adviser at the
end of the fiscal year.

LONG-TERM PERFORMANCE OVERVIEW
An annual  review of a mutual  fund's  record  should also include a look at its
longer-term performance.  The table below presents the average annual returns of
Windsor  Fund and its  comparative  benchmarks  for the past ten years.  It also
presents the results of hypothetical  $10,000  investments  made a decade ago in
the fund,  the  average  fund in its peer  group,  the S&P 500 Index and the S&P
500/BARRA Value Index.
     Although Windsor Fund's 12.5% average annual return for the past decade was
generous in comparison  with  long-term  stock market  returns,  it was modestly
short of the  13.4%  return  for its  average  peer,  and well shy of the  truly
amazing  17.8% return  chalked up by the  unmanaged  S&P 500 Index.  In part, we
trailed the index  because the past ten years were a  growth-stock  decade:  the
growth stocks  within the S&P 500 posted  average  returns of 19.9% a year,  far
ahead of the 15.4% return of the index's value stocks.
     However, even allowing for the disparity in growth and value stock returns,
our performance has been subpar.  All of us on the Windsor Fund team are focused
on improving  our  performance  relative to our primary  benchmark,  the S&P 500
Index.  Our goal is to provide superior returns over the long term, and while we
have  fallen  short of this  goal of  late,  we  continue  to  believe  that our
disciplined  value-investing  approach  and low  operating  costs give us a good
chance to accomplish it in the years ahead.  Our annual  expenses in fiscal 1999
amounted to a slender 0.28% of average assets, more than a full percentage point
below the 1.38% expense ratio for the average multi-cap value fund, according to
Lipper.  We expect this  advantage to aid us, year after year,  in our effort to
provide superior returns.

- ------------------------------------------------------------
                                      TOTAL RETURNS
                             10 YEARS ENDED OCTOBER 31, 1999
- ------------------------------------------------------------
                                 AVERAGE    FINAL VALUE OF
                                 ANNUAL       A $10,000
                                 RATE     INITIAL INVESTMENT
- ------------------------------------------------------------
Vanguard Windsor Fund            12.5%         $32,344
- ------------------------------------------------------------
Average Multi-Cap Value Fund     13.4%         $35,087
- ------------------------------------------------------------
S&P 500 Index                    17.8%         $51,526
- ------------------------------------------------------------
S&P 500/BARRA Value Index        15.4%         $41,790
- ------------------------------------------------------------

     Keep in mind that the returns earned by  stocks--particularly  large growth
stocks--over the past decade were high by historical standards and will probably
be  lower  in the  future.  This  is not a  prediction,  but  rather  a  prudent
assumption that investors should

                                       3
<PAGE>

incorporate  into their  plans,  given that the  long-term  average  return from
stocks is about 11%  annually.  It's worth  noting that this  long-term  average
includes lean years as well as the fabulous gains of the 1990s.

IN SUMMARY
The U.S. stock market provided another big gain for investors during the past 12
months,  which  marked the fifth  fiscal year in a row during  which the S&P 500
Index  returned  more than 20%.  There has never been a streak like it in market
history. Such outsized rewards have pushed stock valuations to very high levels,
reflecting the superb  economic and business  conditions  that have prevailed in
recent years,  as well as  widespread  expectations  for more of the same.  It's
important to  recognize,  however,  that such high  valuations  carry high risk,
should future results fail to match expectations.
     Given  the  risk  of wide  short-term  fluctuations  in  returns  from  the
financial markets,  I repeat our longstanding  advice that investors should hold
balanced  portfolios  of both value and growth  stock  funds,  bond  funds,  and
short-term  reserves  in  proportions  suitable  to their  own  investment  time
horizon, goals, and financial situation. Such diversification can lessen some of
the jolts you're sure to encounter on the road toward your financial  goals.  In
short, I advise preparing an investment plan and sticking with it.

/S/
John J. Brennan

Chairman and Chief Executive Officer
November 11, 1999

================================================================================
A NOTE OF THANKS TO OUR FOUNDER
================================================================================
As you may have read on the inside  cover of our report,  our  founder,  John C.
Bogle,  is retiring  December  31, 1999,  as Senior  Chairman of our Board after
nearly 25 years of devoted  service to Vanguard and our  shareholders.  Vanguard
investors  have Jack to thank for  creating a truly  mutual  mutual fund company
that operates solely in the interest of its fund  shareholders.  And mutual fund
investors  everywhere have benefited from his energetic  efforts to improve this
industry.  Finally, on a personal note, I am forever grateful to Jack for giving
me the opportunity to join this great company in 1982.

                                       4
<PAGE>
A REPORT ON YOUR FUND'S AFTER-TAX RETURNS
Beginning  with this annual  report,  Vanguard is pleased to provide a review of
Windsor Fund's after-tax  performance.  The figures on this page demonstrate the
considerable  impact that federal  income taxes can have on a fund's  return--an
important  consideration for investors who own mutual funds in taxable accounts.
While the pretax  return is most often used to tally a fund's  performance,  the
fund's  after-tax  return,  which accounts for taxes on distributions of capital
gains and income dividends,  is a better  representation of the return that many
investors actually received.  IF YOU OWN WINDSOR FUND IN A TAX-DEFERRED  ACCOUNT
SUCH AS AN INDIVIDUAL  RETIREMENT ACCOUNT OR A 401(K), THIS INFORMATION DOES NOT
APPLY TO YOU. SUCH ACCOUNTS ARE NOT SUBJECT TO CURRENT TAXES.
     The table below presents the pretax and after-tax returns for your fund and
an appropriate peer group of mutual funds. Two things to keep in mind:
     o The after-tax return calculations use the top federal income tax rates in
effect at the time of each  distribution.  The tax burden,  therefore,  would be
somewhat  less, and the after-tax  return  somewhat more, for those in lower tax
brackets.
     o The  peer  funds'  returns  are  based  on data  from  Morningstar,  Inc.
(Elsewhere in this report,  returns for comparable  funds are based on data from
Lipper Inc., which differ somewhat.)
     As you can see,  Windsor  Fund's  pretax  total  return of 13.7% for the 12
months ended  October 31, 1999,  was reduced by taxes to 11.4%.  In other words,
for investors in the highest tax bracket,  taxes cut the fund's pretax return by
2.3 percentage  points.  In comparison,  the average mid-cap value fund earned a
pretax  return of 8.7% and an  after-tax  return of 6.6%,  a  difference  of 2.1
percentage points.

- --------------------------------------------------------------------------------
                              AVERAGE ANNUAL RETURNS: PRETAX AND AFTER-TAX
                                     PERIODS ENDED OCTOBER 31, 1999
                        --------------------------------------------------------
                             1 YEAR             5 YEARS            10 YEARS
                        ------------------  -----------------  -----------------
                         PRETAX  AFTER-TAX  PRETAX  AFTER-TAX  PRETAX  AFTER-TAX
- --------------------------------------------------------------------------------
Windsor Fund               13.7%    11.4%     15.8%    11.9%    12.5%     9.0%
Average Mid-Cap Value Fund* 8.7      6.6      14.6     11.4     12.1      9.6
- --------------------------------------------------------------------------------
*Based on data from Morningstar, Inc.

     Over the past decade,  Windsor Fund's pretax returns  exceeded those of the
average fund in Morningstar's mid-cap value category before taxes, but not after
taxes. For the ten years ended October 31, 1999,  Windsor slightly  outpaced its
average peer, but lost more to taxes (3.5 percentage points) than its peer-group
average (2.5 points).
     We stress that because many interrelated  factors affect how tax-friendly a
fund may be,  it's very  difficult  to  predict  tax  efficiency.  A fund's  tax
efficiency  can be influenced by its turnover  rate,  the types of securities it
holds,  the accounting  practices it uses when selling shares,  and the net cash
flow it receives.
     Finally, it's important to understand that our calculation does not reflect
the tax effect of your own investment  activities.  Specifically,  you may incur
additional capital gains  taxes--thereby  lowering your after-tax return--if you
decide to sell all or some of your shares.

A  NOTE  ABOUT  OUR   CALCULATIONS:   Pretax  total  returns   assume  that  all
distributions   received  (income  dividends,   short-term  capital  gains,  and
long-term  capital  gains) are  reinvested  in new shares,  while our  after-tax
returns assume that  distributions  are reduced by any taxes owed on them before
reinvestment.  When  calculating  the taxes due, we used the highest  individual
federal  income  tax  rates at the time of the  distributions.  Those  rates are
currently 39.6% for dividends and short-term capital gains and 20% for long-term
capital gains. State and local income taxes were not considered. The competitive
group returns provided by Morningstar are calculated in a manner consistent with
that used for Vanguard funds.

                                       5
<PAGE>
THE MARKETS IN PERSPECTIVE
YEAR ENDED OCTOBER 31, 1999

Caution  followed  exuberance  in the U.S.  stock market  during the fiscal year
ended October 31, 1999.  Improving economic  conditions during the first half of
the year set off a raucous  rally from the lows of summer 1998,  when fears of a
global  economic slump swept world markets.  However,  during the second half of
the fiscal  year,  interest  rates kept  rising,  pulling  down bond  prices and
tempering the stock market's optimism. The notion of a global slump was replaced
by worries  that  economic  growth  might be so strong as to threaten a surge in
inflation.

U.S. STOCK MARKETS
A booming U.S. economy and solid increases in corporate earnings lifted the U.S.
stock market,  especially during the first half of the fiscal year. The nation's
economic output increased by about 4% during the year. Consumer spending,  which
accounts for roughly  two-thirds of economic  activity,  powered the  expansion.
Americans spent virtually every dollar they earned,  encouraged by rising wealth
from a long bull market,  plentiful employment,  and rising incomes.  (After-tax
personal  income rose about 5% during the year;  unemployment  fell to a 30-year
low of 4.1% of the workforce in October.)

- --------------------------------------------------------------------------------
                                                     AVERAGE ANNUAL RETURNS
                                                PERIODS ENDED OCTOBER 31, 1999
                                              ----------------------------------
                                                1 YEAR      3 YEARS      5 YEARS
- --------------------------------------------------------------------------------
STOCKS
  S&P 500 Index                                 25.7%        26.5%         26.0%
  Russell 2000 Index                            14.9          9.4          12.6
  Wilshire 5000 Index                           25.7         23.8          23.8
  MSCI EAFE Index                               23.4         12.5           9.5
- --------------------------------------------------------------------------------
BONDS
  Lehman Aggregate Bond Index                    0.5%         6.2%          7.9%
  Lehman 10 Year Municipal Bond Index           -1.2          5.2           7.0
  Salomon Smith Barney 3-Month
    U.S. Treasury Bill Index                     4.6          5.0           5.2
- --------------------------------------------------------------------------------
OTHER
  Consumer Price Index                           2.6%         2.0%          2.4%
- --------------------------------------------------------------------------------
     From October 31, 1998, through April 30, 1999, the stock market rose 22.8%,
as  measured by the  Wilshire  5000 Total  Market  Index.  Investor  confidence,
already  high due to the  booming  economy,  was  bolstered  by easier  monetary
policy--the  Federal Reserve cut short-term  interest rates in November 1998 for
the third time in less than two months.  But by summer, the Fed reversed course,
twice boosting its target for short-term  interest rates to slow the economy and
reduce inflationary pressures.
     Higher interest rates helped take the steam out of the stock market's rally
during the second half of the fiscal  year,  even though  estimates of corporate
earnings kept rising.  Higher rates tend to hurt stocks  because many  investors
use current interest rates to discount the value of a stock's projected earnings
and dividends. The higher the rate, the more future earnings are discounted, and
the less investors will pay for the stock now. After a second-half gain of 2.3%,
the Wilshire 5000 Index recorded a 25.7% return for the full fiscal year.
     Big stocks  outperformed  small  stocks in fiscal 1999,  and growth  stocks
outpaced   value   stocks.   The  S&P  500   Index,   which  is   dominated   by
large-capitalization  stocks,  gained 25.7%,

                                       6
<PAGE>
while the small-cap Russell 2000 Index was up 14.9%.  Growth  stocks--whose high
prices in  relation  to  earnings,  book  value,  and  dividends  indicate  high
expectations  for future  growth--lost  none of their  appeal,  despite  soaring
valuations for many. Both large- and small-cap growth issues gained roughly 30%,
while  value  stocks  within  the S&P 500 Index were up 19.0%,  and the  Russell
2000's value stocks had a scant 0.7% return.
     The  growth/value  gap was due  partly  to the  incredible  performance  of
technology stocks, most of which are classified as growth issues. Within the S&P
500 Index, tech stocks gained 67% during the fiscal year.  Advances of about 30%
were  recorded by retailers and other  consumer-discretionary  stocks and by the
utilities sector,  where gains were concentrated in  telecommunications  stocks.
The only sector with a loss was consumer staples (-8%),  where food and beverage
company stocks suffered from falling profits.
     Other laggards were the auto & transportation  sector (+6%) and health-care
stocks (+9%).

U.S. BOND MARKETS
Rapid  economic  growth was a help to the stock market but a hindrance to bonds.
Investors  worried that,  with  unemployment so low, growth above the 2.5% to 3%
range would cause wages and prices to accelerate.  Indeed,  inflation did rise a
bit,  although the Consumer  Price Index was up a relatively  modest 2.6% during
the 12-month period.
     As mentioned, the Fed sought to combat inflationary pressures by increasing
short-term  interest rates by a quarter-point on June 30 and again on August 24.
The bond market was already  pushing up rates well before the Fed acted.  Yields
of long-term U.S.  Treasury  bonds began rising  significantly  in February.  By
fiscal  year-end,  the 30-year  Treasury  bond's yield was 6.16%, up precisely 1
percentage point for the year. The 10-year Treasury's yield rose 1.41 percentage
points,  from 4.61% to 6.02%.  Short-term interest rates didn't rise as far, and
3-month Treasury bill yields were up 0.77 point to 5.09% at fiscal year-end.
     Rising  interest  rates mean lower  prices for existing  bonds,  of course.
Price declines were higher for  longer-term  bonds,  which are most sensitive to
changing  rates.  For the  taxable  bond  market as a whole,  as measured by the
Lehman Aggregate Bond Index,  prices fell -5.7%,  resulting in a total return of
just 0.5% for the  fiscal  year.  High-yield  (junk)  bonds and  mortgage-backed
securities posted higher returns than Treasuries.

INTERNATIONAL STOCK MARKETS
International  markets  soared in local  currencies  during the 12 months  ended
October  31,  with  European  stocks  gaining  22.7% and  Pacific-region  stocks
advancing 37.8%. The U.S. dollar rose in value against most European  currencies
but fell  against the  Japanese  yen.  For U.S.  investors,  the upshot of these
currency  fluctuations  was to trim returns from Europe to 12.7% in dollar terms
and to boost returns from the Pacific to 50.5%.
     In the major developed  international markets, U.S. investors earned 23.4%,
as measured by the Morgan Stanley Capital International Europe, Australasia, Far
East (EAFE)  Index.  The bull  markets in most  nations  stemmed  from a renewed
appetite  for  risk on the  part of  investors  encouraged  by  clear  signs  of
expanding business activity and generally easier monetary policy.  Japan and the
rest of Asia, which were hit hardest by currency and economic crises in 1997 and
1998, saw the biggest gains.  In Japan,  massive  government  spending  programs
appeared to be working--at  least in the short run--to lift that nation out of a
recession.
     Emerging  markets,  as measured by the Select Emerging  Markets Free Index,
gained 34.1% for U.S.  investors,  as local  returns of better than 70% were cut
nearly in half by weaker currencies in Latin America and eastern Europe.

                                       7
<PAGE>
REPORT FROM WELLINGTON MANAGEMENT
COMPANY, LLP

Vanguard  Windsor  Fund's 13.7% return  during the fiscal year ended October 31,
1999,  was ahead of the 11.7%  return of the  average  multi-cap  value fund but
behind  returns of both the S&P 500 Index (25.7%) and its value  component,  the
S&P 500/BARRA Value Index (19.0%).
     We continue to invest as we have in the past.  Our  approach is to look for
good  companies  that the market has  misappraised  for some  reason,  that have
price/earnings  (P/E)  ratios  below  the  market's,  and  that  have an  upside
appreciation  potential of at least 30%. We make commitments only after thorough
research and careful deliberation, and we then follow closely everything we own.
The P/E ratio of our portfolio (and of the fund as a whole) is distinctly  below
the  market's,   usually  by  about   one-third.   Yet  our  prospective   total
return--which we define as 5-year earnings growth and dividend  yield--is within
10%-15% of the market's. That is our value proposition.
     We buy stocks when we think they are  undervalued,  sell them when they get
to fair value, and replace them with new undervalued names. We are not afraid to
concentrate  when it  makes  sense  and  when,  having  done our  homework,  our
conviction is strong. Our goal is to provide returns on your investment that are
out of the ordinary, without taking undue risks. "Closet indexing"--aligning the
portfolio with a market index--is not consistent with this objective.
     All this  makes for a  portfolio  that is very  different  from the S&P 500
Index. The current  portfolio is overweight in selected  commodity and materials
producers--energy,aluminum,  paper, and specialty chemicals--with holdings equal
to about 25% of the portfolio  versus about 9% of the S&P 500. These stocks hurt
us in fiscal  1998,  but helped in 1999.  Alcoa,  which gained about 55%, is our
largest holding in this phalanx and the third-largest  holding in our portion of
the fund, at 51/2% of the portfolio.  These stocks shot up in April and May, and
the market has been digesting  those gains since.  But we see another upward leg
or two ahead,  if our forecast for global  economic growth of 3.5% for next year
is right.  Our  energy  fortunes  are,  importantly,  also tied to the  domestic
natural gas market, where we see strong fundamentals--demand  growing 2% a year,
a supply base that has peaked out, and a market that will need higher  prices to
bring supply into balance with demand.
     We also have an outsize  position in financial  services--banks,  savings &
loans, specialty finance, and some insurance--where our portfolio's weighting is
24% versus 16% for the S&P 500 Index.  Again, these stocks lagged in 1998, which
we used as an opportunity  to buy more.  This paid off in 1999;  Citigroup,  the
fund's biggest  holding at 6.5% of assets,  was up about 75%. We still see a lot
of value in selected financials,  such as Associates First, a new 2.2% stake for
the fund in a  well-managed,  15%-a-year  grower  selling  at only 15 times next
year's earnings.
- --------------------------------------------------------------------------------
INVESTMENT PHILOSOPHY
The fund reflects a belief that  superior  long-term  investment  results can be
achieved by emphasizing common stocks that are generally  misunderstood,  out of
favor, or undervalued by fundamental  measures such as  price/earnings  ratio or
dividend  yield.  The fund may  concentrate  a large  portion of assets in those
securities or industries the advisers believe offer the best return potential.
- --------------------------------------------------------------------------------
     We own no consumer  nondurables--food,  household products,  beverages, and
tobacco--which  make up

                                       8
<PAGE>

nearly 10% of the S&P 500.  This void  served us well in fiscal  1999,  as these
stocks  lagged the  market by about 30  percentage  points.  Such  companies  as
Coca-Cola,  Procter & Gamble,  and Gillette are still  trading at 25 to 40 times
earnings while offering  long-term  growth prospects on the order of 10% to 12%.
This seems pricey to us, and so we still have nothing in this sector.
     The  other  big   sector   difference   between   us  and  the   market  is
technology--which  makes up 6% of our portfolio  versus 21% of the market.  This
disparity was a significant  negative in 1999, because the tech piece of the S&P
500 Index was up 67%,  accounting  for more than half of the index's 25.7% gain.
Our tech weighting is low for good valuation  reasons.  Our view is that the P/E
multiples--from  40 to 70  times  earnings--sported  by a number  of large  tech
stocks are built on investor  expectations that will be difficult to live up to.
An old rule of thumb is that growth  stocks' P/E ratios  should be roughly twice
the stocks'  growth  rates.  This  suggests that these large tech stocks need to
grow at 20% to 35% on a long-term basis to justify their  multiples.  Given that
U.S. information  technology spending is growing at 11% a year, we expect to see
a lot of  potholes  in the  technology  landscape  in the next 12 months as some
companies  "fall  short" of  expectations  and their stocks  correct.  When tech
stocks  correct,  they  tend to come  down  hard,  and we may  get  some  buying
opportunities.  If we're  going to close our large gap versus the S&P 500's tech
weighting,  we want to do so on our terms.  A recent  instance was IBM, where we
grabbed a new  position of nearly 2% of assets when the company  suggested  that
Y2K  distortions  would hurt earnings for the next two  quarters.  We paid about
211/2 times earnings for this 15% grower, which also pays a 0.5% dividend yield;
its P/E-to-total-return ratio of 1.4 is well below the market's 1.9 ratio.
     Our portion of the fund continues to be highly  concentrated,  with the ten
largest  holdings  totaling 41% of assets.  Our overall  portfolio  P/E of 15.1,
based on estimated year 2000 earnings, is 63% of the market's 23.9 P/E multiple.
By way of  comparison,  our  projected  total return is 12.4%,  about 90% of the
market's  projected  return.  We have  been  looking  for,  and  finding,  solid
double-digit growers, with P/E-to-total-return ratios well below average for the
market. Besides Associates First and IBM, these are TJX Companies,  Ross Stores,
Air Products, MCI WorldCom, and Pharmacia & Upjohn--names that account for about
12% of the  portfolio.  The dedicated  Windsor team that I am proud to lead will
continue  to  forage,  in  our  usual  entrepreneurial  style,  for  undervalued
situations that can add to the  portfolio's  already  considerable  appreciation
potential.

Charles T. Freeman, Portfolio Manager
November 16, 1999

                                       9
<PAGE>
REPORT FROM SANFORD C. BERNSTEIN & CO., INC.

When  Sanford C.  Bernstein & Co. began  managing a portion of Vanguard  Windsor
Fund on June 1, we saw enormous opportunities in an unusually bifurcated market.
Prices for traditional cyclical companies, particularly commodity producers, had
fallen  sharply  over the  previous  two years  because  investors  feared  that
earnings   shortfalls  due  to  the  spread  of  the  Asian  crisis  would  last
indefinitely.  At the same time,  euphoria  surrounding the Internet was lifting
technology and  telecommunications  stock prices to extraordinarily high levels,
and a handful of very large,  very  expensive  stocks were  driving  most of the
market's rally.
     We positioned the portfolio to capture the deep values we saw in cyclicals,
particularly the commodity  producers and railroads.  We also saw opportunity in
health  maintenance  organizations  (HMOs)  and in  retail,  food,  and  tobacco
companies.  Although growth stocks have continued to outperform, the outlook for
value  stocks has become very  strong--indeed,  even better than we  anticipated
when we initiated these positions.
     Economic  growth  has  been  surprisingly  strong  around  the  globe,  and
inventories have shrunk for many commodities.  As a result, commodity prices are
rising,  as are consensus  earnings  expectations  for many of our holdings.  In
several cases,  third-quarter  earnings reports significantly beat expectations.
At the same time, an extraordinary  burst of restructuring  activity and mergers
has increased the long-term earnings power of many commodity  producers we hold.
For example, Dow Chemical's acquisition of Union Carbide this summer is creating
a global  behemoth  with  enormous  opportunities  to cut costs and to  increase
revenues  through  cross-selling a more complete product line to both companies'
customers.  We also see  large  opportunities  in  railroad  companies  that are
smoothing  out  operational  difficulties  that arose from  strategically  sound
mergers.  Railroads  should  benefit as freight  volumes  recover from declining
sales to Asia.
     Other  opportunities  are more  insulated from global  considerations.  HMO
stocks recently fell because of concern about adverse political developments and
possible  class-action  lawsuits.  In our view, it is highly  unlikely that such
suits will  withstand  court  scrutiny,  and the  industry  appears able to pass
through to consumers the costs of regulatory changes;  indeed,  pricing power is
finally returning to the industry. These stocks offer exceptional value.
     Our  portion  of  Windsor   Fund  has  no   holdings  in  the   high-priced
semiconductor and Internet industries, and few in computer software or services.
One very attractive  company in the hardware and peripherals  segment is Seagate
Technology,  a maker of disk drives that has recovered its market leadership and
gained a  compelling  cost  advantage;  as a result,  it is the only  disk-drive
manufacturer with current profits.
     Overall,  the  value  opportunities  we see today  are the  largest  in our
experience.  We expect  improvement in both forecast and reported earnings to be
the catalyst for stock price gains.  Such  improvement is now appearing for some
of our holdings, increasing our confidence in our current strategy.

Marilyn G. Fedak, Portfolio Manager
Steven Pisarkiewicz, Portfolio Manager

November 10, 1999
                                       10
<PAGE>
PERFORMANCE SUMMARY
WINDSOR FUND

All of the data on this page represent past performance, which cannot be used to
predict  future returns that may be achieved by the fund.  Note,  too, that both
share  price and  return  can  fluctuate  widely.  An  investor's  shares,  when
redeemed, could be worth more or less than their original cost.

- --------------------------------------------------------------------------------
TOTAL INVESTMENT RETURNS: OCTOBER 31, 1979-OCTOBER 31, 1999
                                 WINDSOR FUND                          S&P 500
- --------------------------------------------------------------------------------
FISCAL            CAPITAL           INCOME           TOTAL             TOTAL
YEAR              RETURN            RETURN           RETURN            RETURN
- --------------------------------------------------------------------------------
1980              17.2%             7.0%             24.2%             32.1%
1981              11.1              6.9              18.0               0.6
1982              14.2              7.0              32.6              27.8
1984               9.6              6.9              16.5               6.3
1985              16.6              6.7              23.3              19.4
1986              22.8              6.5              29.3              33.2
1987               2.7              1.9               4.6               6.4
1988              18.9              8.1              27.0              14.8
1989              11.9              5.2              17.1              26.4
- --------------------------------------------------------------------------------
                                 WINDSOR FUND                          S&P 500
- --------------------------------------------------------------------------------
FISCAL            CAPITAL           INCOME           TOTAL             TOTAL
YEAR              RETURN            RETURN           RETURN            RETURN
- --------------------------------------------------------------------------------
1990             -31.8%             3.9%            -27.9%             -7.5%
1991              35.7              9.0              44.7              33.5
1992               4.3              5.0               9.3              10.0
1993              24.6              3.7              28.3              14.9
1994               3.7              2.6               6.3               3.9
1995              14.2              3.6              17.8              26.4
1996              19.6              3.6              23.2              24.1
1997              24.3              2.7              27.0              32.1
1998              -2.0              1.2              -0.8              22.0
1999              12.1              1.6              13.7              25.7
- --------------------------------------------------------------------------------
See  Financial  Highlights  table  on page 20 for  dividend  and  capital  gains
information for the past five years.

CUMULATIVE PERFORMANCE: OCTOBER 31, 1989-OCTOBER 31, 1999
[MOUNTAIN CHART]
- --------------------------------------------------------------------------------
                                      AVERAGE
                         WINDSOR      MULTI-CAP     S&P 500
                         FUND         VALUE FUND*   INDEX
- --------------------------------------------------------------------------------
         1989/10         10000         10000         10000
         1990/01          9038          9630          9747
         1990/04          9002          9662          9882
         1990/07          9261         10204         10738
         1990/10          7207          8702          9252
         1991/01          8813         10013         10566
         1991/04          9776         10947         11623
         1991/07         10045         11342         12108
         1991/10         10428         11764         12351
         1992/01         10784         12363         12963
         1992/04         11416         12586         13253
         1992/07         11813         12825         13656
         1992/10         11398         12921         13581
         1993/01         12974         13873         14334
         1993/04         13311         14101         14478
         1993/07         13977         14527         14849
         1993/10         14622         15444         15610
         1994/01         15554         16034         16180
         1994/04         14511         15235         15248
         1994/07         15347         15445         15615
         1994/10         15550         16009         16214
         1995/01         14927         15694         16266
         1995/04         16473         17072         17911
         1995/07         18365         18668         19692
         1995/10         18318         19288         20501
         1996/01         19599         20874         22555
         1996/04         20845         21764         23323
         1996/07         20304         20995         22954
         1996/10         22561         23267         25441
         1997/01         25564         25522         28497
         1997/04         25622         25359         29184
         1997/07         29980         30056         34922
         1997/10         28661         29968         33610
         1998/01         29342         30787         36165
         1998/04         33717         34171         41169
         1998/07         30716         32346         41657
         1998/10         28436         31407         41001
         1999/01         29522         33792         47915
         1999/04         34692         35760         50154
         1999/07         33760         35898         50073
         1999/10         32344         35087         51526

- --------------------------------------------------------------------------------
                            AVERAGE ANNUAL TOTAL RETURNS
                           PERIODS ENDED OCTOBER 31, 1999
                           -------------------------------     FINAL VALUE OF A
                           1 YEAR     5 YEARS     10 YEARS    $10,000 INVESTMENT
- --------------------------------------------------------------------------------
Windsor Fund               13.74%      15.77%       12.46%               $32,344
Average Multi-Cap
         Value Fund*       11.72       16.99        13.37                 35,087
S&P 500 Index              25.67       26.02        17.82                 51,526
- --------------------------------------------------------------------------------
*Derived from data provided by Lipper Inc.
- --------------------------------------------------------------------------------
AVERAGE ANNUAL TOTAL RETURNS: PERIODS ENDED SEPTEMBER 30, 1999*
- --------------------------------------------------------------------------------
                                                             10 YEARS
                  INCEPTION                          ---------------------------
                  DATE          1 YEAR    5 YEARS    CAPITAL    INCOME     TOTAL
- --------------------------------------------------------------------------------
Windsor Fund      10/23/1958    19.36%    15.57%      7.88%      3.64%    11.52%
- --------------------------------------------------------------------------------
*SEC rules require that we provide this average annual total return  information
through the latest calendar quarter.

                                       11
<PAGE>

FUND PROFILE
WINDSOR FUND

This Profile provides a snapshot of the fund's characteristics as of October 31,
1999,  compared where  appropriate to an unmanaged  index.  Key elements of this
Profile are defined on page 13.

PORTFOLIO CHARACTERISTICS
- ---------------------------------------------------------
                                     WINDSOR      S&P 500
- ---------------------------------------------------------
Number of Stocks                         195          500
Median Market Cap                     $13.1B       $72.6B
Price/Earnings Ratio                   17.4x        27.7x
Price/Book Ratio                        2.2x         5.1x
Yield                                   1.6%         1.2%
Return on Equity                       15.0%        23.0%
Earnings Growth Rate                    9.6%        15.0%
Foreign Holdings                       11.4%         1.5%
Turnover Rate                            56%           --
Expense Ratio                          0.28%           --
Cash Reserves                           1.3%           --

INVESTMENT FOCUS
- ---------------------------------------------------------
[GRID]
Style............Value
Market Cap.......Medium

VOLATILITY MEASURES
- ---------------------------------------------------------
                                     WINDSOR      S&P 500
- ---------------------------------------------------------
R-Squared                             0.78           1.00
Beta                                  1.05           1.00

TEN LARGEST HOLDINGS
(% OF TOTAL NET ASSETS)
- ---------------------------------------------------------
Citigroup, Inc.                                      6.5%
AT&T Corp.                                           4.6
Rhone-Poulenc SA                                     4.6
Alcoa Inc.                                           4.3
Bank of America Corp.                                3.1
Columbia/HCA Healthcare Corp.                        2.3
Washington Mutual, Inc.                              2.2
Associates First Capital Corp.                       2.2
Golden West Financial Corp.                          2.1
MCI WorldCom, Inc.                                   2.0
- ---------------------------------------------------------
Top Ten                                             33.9%

SECTOR DIVERSIFICATION (% OF COMMON STOCKS)
- ---------------------------------------------------------
                     OCTOBER 31, 1998   OCTOBER 31, 1999
                     ------------------------------------
                         WINDSOR      WINDSOR     S&P 500
                     ------------------------------------
Auto & Transportation ...  6.4%         7.4%         2.2%
Consumer Discretionary ..  0.8          4.7         12.5
Consumer Staples ........  0.0          1.1          7.2
Financial Services ...... 29.0         29.4         16.1
Health Care .............  7.8          6.9         11.0
Integrated Oils .........  3.5          2.8          5.2
Other Energy ............ 10.3          6.2          1.4
Materials & Processing .. 21.0         21.2          3.2
Producer Durables .......  5.8          3.3          3.3
Technology ..............  5.4          4.8         20.5
Utilities ...............  7.3          9.7         11.2
Other ...................  2.7          2.5          6.2
- ---------------------------------------------------------

                                       12
<PAGE>

BETA. A measure of the magnitude of a fund's past  share-price  fluctuations  in
relation  to the ups and downs of the  overall  market  (or  appropriate  market
index).  The market (or index) is assigned a beta of 1.00, so a fund with a beta
of 1.20  would have seen its share  price  rise or fall by 12% when the  overall
market rose or fell by 10%.

CASH  RESERVES.  The  percentage  of a  fund's  net  assets  invested  in  "cash
equivalents"--highly  liquid,  short-term,   interest-bearing  securities.  This
figure does not include cash  invested in futures  contracts  to simulate  stock
investment.

EARNINGS  GROWTH RATE.  The average  annual rate of growth in earnings  over the
past five years for the stocks now in a fund.

EXPENSE  RATIO.  The  percentage of a fund's  average net assets used to pay its
annual  administrative  and advisory  expenses.  These expenses  directly reduce
returns to investors.

FOREIGN HOLDINGS. The percentage of a fund's equity assets represented by stocks
or American Depositary Receipts of companies based outside the United States.

INVESTMENT  FOCUS.  This  grid  indicates  the  focus  of a fund in terms of two
attributes:  market  capitalization  (large,  medium,  or  small)  and  relative
valuation (growth, value, or a blend).

MEDIAN  MARKET  CAP.  An  indicator  of the  size of  companies  in which a fund
invests;  the  midpoint  of  market   capitalization   (market  price  x  shares
outstanding) of a fund's stocks, weighted by the proportion of the fund's assets
invested  in each  stock.  Stocks  representing  half of the fund's  assets have
market capitalizations above the median, and the rest are below it.

NUMBER OF STOCKS. An indicator of diversification. The more stocks a fund holds,
the more  diversified  it is and the more  likely  to  perform  in line with the
overall stock market.

PRICE/BOOK  RATIO.  The share price of a stock divided by its net worth, or book
value,  per share.  For a fund,  the weighted  average  price/book  ratio of the
stocks it holds.

PRICE/EARNINGS  RATIO.  The ratio of a stock's  current  price to its  per-share
earnings over the past year. For a fund, the weighted  average P/E of the stocks
it holds. P/E is an indicator of market expectations about corporate  prospects;
the higher the P/E, the greater the expectations for a company's future growth.

R-SQUARED.  A measure of how much of a fund's past  returns can be  explained by
the returns from the overall market (or its benchmark  index). If a fund's total
return  were  precisely  synchronized  with the  overall  market's  return,  its
R-squared  would  be 1.00.  If a  fund's  returns  bore no  relationship  to the
market's returns, its R-squared would be 0.

RETURN ON  EQUITY.  The annual  average  rate of return  generated  by a company
during the past five years for each dollar of  shareholder's  equity (net income
divided by  shareholder's  equity).  For a fund, the weighted  average return on
equity for the companies whose stocks it holds.

SECTOR DIVERSIFICATION. The percentages of a fund's common stocks that come from
each of the major industry groups that compose the stock market.

TEN LARGEST  HOLDINGS.  The percentage of net assets that a fund has invested in
its ten largest holdings.  (The average for stock mutual funds is about 35%.) As
this percentage  rises, a fund's returns are likely to be more volatile  because
they are more dependent on the fortunes of a few companies.

TURNOVER  RATE. An indication of trading  activity  during the past year.  Funds
with high turnover rates incur higher  transaction  costs and are more likely to
distribute capital gains (which are taxable to investors).

YIELD.  A snapshot of a fund's  income from interest and  dividends.  The yield,
expressed  as a  percentage  of the fund's net asset  value,  is based on income
earned over the past 30 days and is  annualized,  or  projected  forward for the
coming  year.  The  index  yield  is  based on the  current  annualized  rate of
dividends paid on stocks in the index.

                                       13
<PAGE>
FINANCIAL STATEMENTS
OCTOBER 31, 1999

STATEMENT OF NET ASSETS
This Statement  provides a detailed list of the fund's holdings,  including each
security's market value on the last day of the reporting period.  Securities are
grouped  and  subtotaled  by asset  type  (common  stocks,  bonds,  etc.) and by
industry sector. Other assets are added to, and liabilities are subtracted from,
the value of Total Investments to calculate the fund's Net Assets.  Finally, Net
Assets are divided by the outstanding  shares of the fund to arrive at its share
price, or Net Asset Value (NAV) Per Share.
     At the end of the Statement of Net Assets, you will find a table displaying
the  composition of the fund's net assets on both a dollar and per-share  basis.
Because all income and any realized gains must be  distributed  to  shareholders
each year, the bulk of net assets consists of Paid in Capital (money invested by
shareholders).  The amounts shown for  Undistributed  Net Investment  Income and
Accumulated  Net  Realized  Gains  usually  approximate  the  sums  the fund had
available to distribute to shareholders as income  dividends or capital gains as
of  the  statement  date,  but  may  differ  because   certain   investments  or
transactions  may  be  treated  differently  for  financial  statement  and  tax
purposes.  Any Accumulated  Net Realized  Losses,  and any cumulative  excess of
distributions  over net income or net  realized  gains,  will appear as negative
balances.  Unrealized Appreciation  (Depreciation) is the difference between the
market value of the fund's  investments  and their cost,  and reflects the gains
(losses) that would be realized if the fund were to sell all of its  investments
at their statement-date values.
- --------------------------------------------------------------------------------
                                                                          MARKET
                                                                          VALUE*
WINDSOR FUND                                          SHARES               (000)
- --------------------------------------------------------------------------------
COMMON STOCKS (96.7%)+
- --------------------------------------------------------------------------------
AUTO & TRANSPORTATION (7.2%)
     Compagnie Generale des
          Etablissements Michelin
          Class B                                  6,000,586             261,106
     Canadian National
          Railway Co.                              5,042,100             153,784
     Eaton Corp.                                   2,015,900             151,696
     Delta Air Lines, Inc.                         2,301,522             125,289
o(1) America West Holdings Corp.
          Class B                                  3,484,500              72,086
     Burlington Northern
          Santa Fe Corp.                           1,869,000              59,574
     Union Pacific Corp.                           1,059,300              59,056
     General Motors Corp.                            722,100              50,728
     Delphi Automotive
          Systems Corp.                            2,937,059              48,278
     Norfolk Southern Corp.                        1,923,600              47,008
     CSX Corp.                                     1,124,000              46,084
     TRW, Inc.                                       909,000              38,973
     Genuine Parts Co.                             1,486,500              38,742
     Ford Motor Co.                                  578,800              31,762
     Dana Corp.                                      886,200              26,198
                                                                      ----------
                                                                       1,210,364
                                                                      ----------
CONSUMER DISCRETIONARY (4.6%)
     May Department Stores Co.                     4,737,800             164,342
(1)  Ross Stores, Inc.                             6,509,600             134,261
o    Republic Services, Inc.
          Class A                                  8,091,500              99,121
o    BJ's Wholesale Club, Inc.                     2,224,800              68,552
     TJX Cos., Inc.                                1,928,200              52,302
- --------------------------------------------------------------------------------
                                                                          MARKET
                                                                           VALUE
                                                      SHARES               (000)
- --------------------------------------------------------------------------------
o    Federated Department
          Stores, Inc.                             1,100,300              46,969
     Whirlpool Corp.                                 619,800              43,192
o    Jones Apparel Group, Inc.                     1,182,900              37,409
     VF Corp.                                        994,300              29,891
     Mattel, Inc.                                  2,231,300              29,844
     Sears, Roebuck & Co.                            841,800              23,728
o    Saks Inc.                                     1,239,100              21,297
     Dillard's Inc.                                  616,900              11,644
o(1) HomeBase, Inc.                                2,307,100               8,796
                                                                      ----------
                                                                         771,348
                                                                      ----------

CONSUMER STAPLES (1.1%)
     Philip Morris Cos., Inc.                      2,502,900              63,042
     ConAgra, Inc.                                 2,175,800              56,707
     Tyson Foods, Inc.                             1,812,600              27,642
     SuperValu Inc.                                  942,100              19,784
     IBP, Inc.                                       736,500              17,630
                                                                      ----------
                                                                         184,805
                                                                      ----------
FINANCIAL SERVICES (28.4%)
     BANKS--NEW YORK CITY (0.2%)
     The Chase Manhattan Corp.                       197,800              17,283
     J.P. Morgan & Co., Inc.                          99,900              13,074

     BANKS--OUTSIDE NEW YORK CITY (7.2%)
     Bank of America Corp.                         8,017,971             516,157
     National City Corp.                           5,172,800             152,598
     UnionBanCal Corp.                             3,213,000             139,565
     U.S. Bancorp                                  3,643,900             135,052
     Fleet Boston Corp.                            2,009,530              87,666
     Bank One Corp.                                2,220,900              83,423
     First Union Corp.                             1,944,300              82,997
     Regions Financial Corp.                         583,200              17,532

                                       14
<PAGE>
- --------------------------------------------------------------------------------
                                                                          MARKET
                                                                          VALUE*
                                                      SHARES               (000)
- --------------------------------------------------------------------------------
     DIVERSIFIED FINANCIAL SERVICES (6.8%)
     Citigroup, Inc.                              20,353,400           1,101,628
     American General Corp.                          637,000              47,257

     FINANCIAL MISCELLANEOUS (2.8%)
     Associates First Capital Corp.               10,034,900             366,274
     MBIA, Inc.                                      803,800              45,867
     AMBAC Financial Group Inc.                      579,900              34,649
     Fannie Mae                                      344,600              24,380

     INSURANCE--MULTI-LINE (3.5%)
     CIGNA Corp.                                   3,945,800             294,949
     Allstate Corp.                                7,075,400             203,418
     American International
          Group, Inc.                                472,100              48,597
     Torchmark Corp.                               1,061,800              33,115
     Horace Mann Educators Corp.                     257,300               7,253
     Old Republic International Corp.                383,800               5,253

     INSURANCE--PROPERTY-CASUALTY (0.8%)
     PartnerRe Ltd.                                1,860,500              58,024
     The Chubb Corp.                                 907,500              49,799
     IPC Holdings Ltd.                             1,649,800              28,047

REAL ESTATE INVESTMENT TRUST (2.8%)
     Archstone Communities
          Trust REIT                               5,541,600             110,832
(1)  Liberty Property Trust REIT                   4,440,500             103,797
     Equity Residential Properties
          Trust REIT                               2,370,900              99,133
     Spieker Properties, Inc. REIT                 1,292,300              45,150
     CarrAmerica Realty Corp. REIT                 1,372,400              30,536
     Duke Realty Investments,
          Inc. REIT                                1,357,100              26,633
     Avalonbay Communities,
          Inc. REIT                                  796,336              25,732
     Camden Property Trust REIT                      870,000              23,544

     SAVINGS & LOAN (4.3%)
     Washington Mutual, Inc.                      10,216,664             367,161
(1)  Golden West Financial Corp.                   3,145,100             351,465
                                                                      ----------
                                                                       4,777,840
                                                                      ----------
HEALTH CARE (6.7%)
     Columbia/HCA
Healthcare Corp.                                  16,020,800             386,502
     Aetna Inc.                                    3,560,000             178,890
     Pharmacia & Upjohn, Inc.                      3,201,600             172,686
o    Tenet Healthcare Corp.                        6,792,800             132,035
o(1) PacifiCare Health Systems, Inc.               2,619,300             103,299
     American Home Products Corp.                    976,400              51,017
o(1) Foundation Health Systems
          Class A                                  6,028,660              39,940
o(1) LifePoint Hospitals, Inc.                     2,032,189              24,005
o(1) Triad Hospitals, Inc.                         2,170,789              21,165
     Bergen Brunswig Corp.
          Class A                                  1,017,100               7,247
     Rhone-Poulenc SA Class A                         99,671               5,573
                                                                    ------------
                                                                       1,122,359
                                                                    ------------
- --------------------------------------------------------------------------------
                                                                          MARKET
                                                                          VALUE*
                                                      SHARES               (000)
- --------------------------------------------------------------------------------
INTEGRATED OILS (2.7%)
     USX-Marathon Group                            4,897,700             142,646
     Exxon Corp.                                   1,529,200             113,256
     Occidental Petroleum Corp.                    2,623,200              59,842
     Shell Transport & Trading
          Co. ADR                                  1,302,300              59,743
     Phillips Petroleum Co.                        1,105,400              51,401
     Mobil Corp.                                     253,200              24,434
                                                                         451,322
OTHER ENERGY (6.0%)
     Burlington Resources, Inc.                    6,729,800             234,702
     Anderson Exploration Ltd.                    11,672,400             150,379
     Ultramar Diamond
          Shamrock Corp.                           4,547,400             111,411
     Union Pacific Resources
          Group, Inc.                              7,333,900             106,342
     Transocean Offshore, Inc.                     3,434,200              93,367
     Anadarko Petroleum Corp.                      2,636,300              81,231
(1)  Valero Energy Corp.                           3,635,300              66,799
     Alberta Energy Co. Ltd.                       1,411,100              43,039
(1)  Cabot Oil & Gas Corp. Class A                 2,409,500              38,853
     Tosco Corp.                                   1,279,300              32,382
     Devon Energy Corp.                              556,475              21,633
     Ashland, Inc.                                   607,000              20,031
o(1) EEX Corp.                                     4,148,499              15,298
                                                                      ----------
                                                                       1,015,467
                                                                      ----------
MATERIALS & PROCESSING (20.4%)
     Rhone-Poulenc SA ADR                         13,748,650             763,050
     Alcoa Inc.                                   11,993,834             728,625
     Air Products & Chemicals, Inc.                5,226,500             143,729
(1)  Hercules, Inc.                                5,500,600             132,358
o    Smurfit-Stone Container Corp.                 5,825,850             125,984
     Sigma-Aldrich Corp.                           4,326,800             123,314
     Engelhard Corp.                               6,276,900             110,630
     Jefferson Smurfit Group
          PLC ADR                                  3,997,541             102,937
     Abitibi-Consolidated, Inc.                    8,081,100              97,478
     Pechiney SA ADR A                             2,721,128              79,083
     International Paper Co.                       1,248,300              65,692
     Dow Chemical Co.                                543,300              64,245
(1)  Phosphate Resources
          Partners LP                              6,302,400              63,418
     Lafarge Corp.                                 1,918,300              56,950
     AK Steel Corp.                                3,167,852              54,843
     Lyondell Chemical Co.                         4,385,903              53,179
     Praxair, Inc.                                 1,108,200              51,808
     Donohue, Inc. Class A                         3,097,600              49,279
     Archer-Daniels-Midland Co.                    3,798,715              46,772
     Bowater Inc.                                    756,680              39,726
     Nucor Corp.                                     732,600              38,004
     Willamette Industries, Inc.                     909,600              37,805
o(1) Kaiser Aluminum &
          Chemical Corp.                           5,789,334              37,269
     Reynolds Metals Co.                             541,600              32,733
o    Owens-Illinois, Inc.                          1,303,800              31,210
     Champion International Corp.                    493,400              28,525
     Temple-Inland Inc.                              467,800              27,191
o(1) Albany International Corp.                    1,695,741              25,754

                                       15
<PAGE>
- --------------------------------------------------------------------------------
                                                                          MARKET
                                                                          VALUE*
WINDSOR FUND                                          SHARES               (000)
- --------------------------------------------------------------------------------
     Crown Cork & Seal Co., Inc.                     986,900              23,624
o    American Standard Cos., Inc.                    591,400              22,584
     Fluor Corp.                                     526,800              21,006
     Sonoco Products Co.                             823,000              19,752
(1)  Century Aluminum Co.                          2,000,000              18,000
     Great Lakes Chemical Corp.                      485,000              17,218
     Boise Cascade Corp.                             473,900              16,883
     Ryerson Tull, Inc.                              625,846              12,830
     CK Witco Corp.                                1,334,129              12,507
     Deltic Timber Corp.                             549,471              12,329
     Cabot Corp.                                     553,300              10,305
     Sherwin-Williams Co.                            460,000              10,293
(1)  Mississippi Chemical Corp.                    1,685,300               9,374
o    Burlington Industries, Inc.                   2,383,700               8,790
     Owens Corning                                   425,900               8,731
     Georgia Pacific Group                           100,000               3,969
     Armstrong World Industries Inc.                  54,300               2,029
                                                                      ----------
                                                                       3,441,815
                                                                      ----------
PRODUCER DURABLES (3.2%)
     Alcatel SA ADR                                3,567,600             109,481
     Case Corp.                                    1,611,500              85,410
o(1) Toll Brothers, Inc.                           3,529,166              61,760
     New Holland NV                                3,865,100              58,701
     Lockheed Martin Corp.                         1,820,900              36,418
     Kaufman & Broad Home Corp.                    1,698,600              34,078
o(1) U.S. Home Corp.                               1,168,495              32,718
     Northrop Grumman Corp.                          552,300              30,307
     Thomas & Betts Corp.                            475,800              21,352
(1)  MDC Holdings, Inc.                            1,156,300              18,067
o(1) Beazer Homes USA, Inc.                          860,464              16,456
     The BFGoodrich Co.                              625,800              14,824
     Centex Corp.                                    464,900              12,465
                                                                      ----------
                                                                         532,037
                                                                      ----------
Technology (4.7%)
     International Business
          Machines Corp.                           2,994,200             294,554
o(1) Arrow Electronics, Inc.                       6,393,100             139,449
o    Quantum Corp.- DLT &
          Storage Systems                          6,525,500             100,737
     Avnet, Inc.                                   1,593,500              86,547
o    Seagate Technology Inc.                       1,473,800              43,385
o    Adaptec, Inc.                                   873,700              39,317
o(1) General Semiconductor, Inc.                   3,468,600              36,420
o    Quantum Corp.-
          Hard Disk Drive                          2,424,000              14,847
     Harris Corp.                                    627,900              14,089
o    Litton Industries, Inc.                         279,900              13,138
     Scientific-Atlanta, Inc.                         49,300               2,822
                                                                      ----------
                                                                         785,305
                                                                      ----------
UTILITIES (9.4%)
     AT&T Corp.                                   16,680,316             779,805
o    MCI WorldCom, Inc.                            3,947,093             338,710
- --------------------------------------------------------------------------------
                                                                          MARKET
                                                                          VALUE*
                                                      SHARES               (000)
- --------------------------------------------------------------------------------
     FirstEnergy Corp.                             1,704,100              44,413
     PG&E Corp.                                    1,919,100              44,019
     Ameren Corp.                                  1,152,100              43,564
     SBC Communications Inc.                         837,720              42,671
     Central & South West Corp.                    1,778,500              39,460
     Bell Atlantic Corp.                             585,800              38,040
     Cinergy Corp.                                 1,334,900              37,711
     New Century Energies, Inc.                    1,065,300              34,689
     GPU, Inc.                                       993,600              33,720
     Allegheny Energy, Inc.                          978,900              31,141
     BellSouth Corp.                                 667,400              30,033
o    MediaOne Group, Inc.                            415,000              29,491
     Alliant Energy Corp.                            607,500              16,516
                                                                      ----------
                                                                       1,583,983
                                                                      ----------
OTHER (2.3%)
     Minnesota Mining &
          Manufacturing Co.                          857,200              81,488
     Cooper Industries, Inc.                         743,900              32,034
     Allegheny Teledyne Inc.                       1,586,200              24,090
     Kemira Oyj ADR                                  628,200               7,758
     Miscellaneous (1.5%)                            250,391             395,761
- --------------------------------------------------------------------------------
TOTAL COMMON STOCKS
     (COST $14,280,126)                                               16,272,406
- --------------------------------------------------------------------------------
PREFERRED STOCK (1.0%)
     News Corp. Ltd. ADR
          (COST $92,778)                           5,957,875             164,214
CONVERTIBLE PREFERRED STOCK (0.1%)
     Kaufman & Broad Home Corp.
          8.25% Cvt. Pfd.
          (COST $23,120)                           3,163,700              22,541
- --------------------------------------------------------------------------------
                                                        FACE
                                                      AMOUNT
                                                       (000)
- --------------------------------------------------------------------------------
TEMPORARY CASH INVESTMENTS (2.1%)+
- --------------------------------------------------------------------------------
FEDERAL HOME LOAN MORTGAGE CORP.
(2)  5.64%, 2/2/2000                                   5,000               4,922
FEDERAL NATIONAL MORTGAGE ASSN.
(2   5.64%, 1/18/2000                                 10,000               9,868
REPURCHASE AGREEMENTS
Collateralized by U.S. Government
     Obligations in a Pooled
     Cash Account
     5.24%, 11/1/1999                                308,125             308,125
     5.26%, 11/1/1999--Note F                         30,270              30,270
- --------------------------------------------------------------------------------
TOTAL TEMPORARY CASH INVESTMENTS
     (COST $353,203)                                                     353,185
- --------------------------------------------------------------------------------
TOTAL INVESTMENTS (99.9%)
     (COST $14,749,227)                                               16,812,346
- --------------------------------------------------------------------------------
                                       16
<PAGE>
- --------------------------------------------------------------------------------
                                                                          MARKET
                                                                          VALUE*
                                                                           (000)
- --------------------------------------------------------------------------------
OTHER ASSETS AND LIABILITIES (0.1%)
- --------------------------------------------------------------------------------
Other Assets--Note C                                                     218,263
Liabilities--Note F                                                    (206,887)
                                                                          11,376
- --------------------------------------------------------------------------------
NET ASSETS (100%)
- --------------------------------------------------------------------------------
Applicable to 994,989,422 outstanding $.001
     par value shares of beneficial interest
     (unlimited authorization)                                       $16,823,722
================================================================================
NET ASSET VALUE PER SHARE                                                 $16.91
================================================================================
*    See Note A in Notes to Financial Statements.
o    Non-Income-Producing  Security.
+    The fund invests a portion of its cash reserves in equity  markets  through
     the  use of  index  futures  contracts.  After  giving  effect  to  futures
     investments,   the  fund's   effective  common  stock  and  temporary  cash
     investment positions represent 97.6% and 1.2%, respectively, of net assets.
     See Note E in Notes to Financial Statements.
(1)  Considered  an  affiliated  company  as the fund  owns  more than 5% of the
     outstanding voting securities of such companies.  The total market value of
     investments in affiliated companies was $1,570,807,000.
(2)  Security segregated as initial margin for open futures contracts.
ADR--American Depositary Receipt.
REIT--Real Estate Investment Trust.
- --------------------------------------------------------------------------------
                                                      AMOUNT                 PER
                                                       (000)               SHARE
- --------------------------------------------------------------------------------
AT OCTOBER 31, 1999, NET ASSETS CONSISTED OF:
- --------------------------------------------------------------------------------
Paid in Capital                                  $12,801,594              $12.87
Undistributed Net
     Investment Income                                93,521                 .09
Accumulated Net
     Realized Gains                                1,859,220                1.87
Unrealized Appreciation--
     Note E
     Investment Securities                         2,063,119                2.07
     Futures Contracts                                 6,268                 .01
- --------------------------------------------------------------------------------
NET ASSETS                                       $16,823,722              $16.91
================================================================================

                                       17
<PAGE>


STATEMENT OF OPERATIONS
This Statement  shows dividend and interest income earned by the fund during the
reporting period,  and details the operating expenses charged to the fund. These
expenses  directly  reduce the amount of investment  income  available to pay to
shareholders  as  dividends.  This  Statement  also  shows  any Net Gain  (Loss)
realized  on the  sale of  investments,  and the  increase  or  decrease  in the
Unrealized Appreciation  (Depreciation) on investments during the period. If the
fund  invested  in futures  contracts  during the  period,  the results of these
investments are shown separately.
- --------------------------------------------------------------------------------
                                                                    WINDSOR FUND
                                                     YEAR ENDED OCTOBER 31, 1999
                                                                           (000)
- --------------------------------------------------------------------------------
INVESTMENT INCOME
INCOME
     Dividends*                                                      $   309,153
     Interest                                                             15,017
     Security Lending                                                      1,232
          Total Income                                                   325,402
EXPENSES
     Investment Advisory Fees--Note B
          Basic Fee                                                       22,023
          Performance Adjustment                                        (14,040)
     The Vanguard Group--Note C
          Management and Administrative                                   38,797
          Marketing and Distribution                                       2,519
     Custodian Fees                                                          498
     Auditing Fees                                                            23
     Shareholders' Reports                                                   408
     Trustees' Fees and Expenses                                              27
          Total Expenses                                                  50,255
          Expenses Paid Indirectly--Note C                               (2,460)
          Net Expenses                                                    47,795
- --------------------------------------------------------------------------------
NET INVESTMENT INCOME                                                    277,607
- --------------------------------------------------------------------------------
REALIZED NET GAIN (LOSS)
     Investment Securities Sold*                                       1,952,962
     Futures Contracts                                                  (12,431)
- --------------------------------------------------------------------------------
REALIZED NET GAIN                                                      1,940,531
- --------------------------------------------------------------------------------
CHANGE IN UNREALIZED APPRECIATION (DEPRECIATION)
     Investment Securities                                                36,551
     Futures Contracts                                                     6,268
- --------------------------------------------------------------------------------
CHANGE IN UNREALIZED APPRECIATION (DEPRECIATION)                          42,819
- --------------------------------------------------------------------------------
NET INCREASE IN NET ASSETS RESULTING FROM OPERATIONS                  $2,260,957
================================================================================
*Dividend   income  and  realized  net  gain  from  affiliated   companies  were
$86,331,000 and $567,678,000, respectively.

                                       18
<PAGE>

STATEMENT OF CHANGES IN NET ASSETS
This Statement shows how the fund's total net assets changed during the two most
recent reporting periods. The Operations section summarizes information detailed
in  the  Statement  of  Operations.   The  amounts  shown  as  Distributions  to
shareholders  from the fund's net  income  and  capital  gains may not match the
amounts shown in the Operations section, because distributions are determined on
a tax  basis  and may be made in a period  different  from the one in which  the
income was earned or the gains were  realized on the financial  statements.  The
Capital Share Transactions section shows the amount shareholders invested in the
fund,  either by purchasing shares or by reinvesting  distributions,  as well as
the amounts redeemed.  The  corresponding  numbers of Shares Issued and Redeemed
are shown at the end of the Statement.
- --------------------------------------------------------------------------------
                                                               WINDSOR FUND
                                                          YEAR ENDED OCTOBER 31,
                                                      --------------------------
                                                           1999             1998
                                                          (000)            (000)
- --------------------------------------------------------------------------------
INCREASE (DECREASE) IN NET ASSETS
OPERATIONS
  Net Investment Income                                277,607          270,099
  Realized Net Gain                                  1,940,531        1,346,037
  Change in Unrealized Appreciation (Depreciation)      42,819       (1,700,942)
  Net Increase (Decrease) in Net Assets
    Resulting from Operations                        2,260,957         (84,806)
DISTRIBUTIONS
  Net Investment Income                               (255,285)        (268,858)
  Realized Capital Gain                             (1,341,486)      (3,045,000)
  Total Distributions                               (1,596,771)      (3,313,858)
CAPITAL SHARE TRANSACTIONS1
  Issued                                             1,402,297        1,632,455
  Issued in Lieu of Cash Distributions               1,504,748        3,148,447
  Redeemed                                          (5,102,907)      (3,704,909)
  Net Increase (Decrease) from Capital Share
    Transactions                                    (2,195,862)       1,075,993
- --------------------------------------------------------------------------------
  Total Decrease                                    (1,531,676)      (2,322,671)
- --------------------------------------------------------------------------------
NET ASSETS
  Beginning of Year                                 18,355,398       20,678,069
  End of Year                                      $16,823,722      $18,355,398
================================================================================
1Shares Issued (Redeemed)
  Issued                                                82,191           92,583
  Issued in Lieu of Cash Distributions                 100,940          187,538
  Redeemed                                            (311,166)        (214,952)
    NetIncrease (Decrease)in Shares Outstanding       (128,035)          65,169
================================================================================

                                       19
<PAGE>
FINANCIAL HIGHLIGHTS
This table  summarizes  the  fund's  investment  results  and  distributions  to
shareholders on a per-share  basis. It also presents the fund's Total Return and
shows net  investment  income and expenses as percentages of average net assets.
These data will help you assess:  the  variability  of the fund's net income and
total returns from year to year;  the relative  contributions  of net income and
capital gains to the fund's total return; how much it costs to operate the fund;
and the extent to which the fund tends to distribute  capital  gains.  The table
also  shows the  Portfolio  Turnover  Rate,  a measure of  trading  activity.  A
turnover  rate of 100% means that the  average  security is held in the fund for
one year.
<TABLE>
<CAPTION>
- -----------------------------------------------------------------------------------------------------------
                                                                               WINDSOR FUND
                                                                         YEAR ENDED OCTOBER 31,
                                                              ---------------------------------------------
<S>                                                               <C>       <C>      <C>      <C>      <C>
FOR A SHARE OUTSTANDING THROUGHOUT EACH YEAR                      1999      1998     1997     1996     1995
- -----------------------------------------------------------------------------------------------------------
NET ASSET VALUE, BEGINNING OF YEAR                              $16.34    $19.55   $16.99   $15.55   $14.55
- -----------------------------------------------------------------------------------------------------------
INVESTMENT OPERATIONS
     Net Investment Income                                         .27       .23      .36      .43      .44
     Net Realized and Unrealized Gain (Loss) on Investments       1.77     (.32)     3.94     2.85     1.86
                                                              ---------------------------------------------
          Total from Investment Operations                        2.04     (.09)     4.30     3.28     2.30
                                                              ---------------------------------------------
DISTRIBUTIONS
     Dividends from Net Investment Income                        (.24)     (.24)    (.41)    (.46)    (.44)
     Distributions from Realized Capital Gains                  (1.23)    (2.88)   (1.33)   (1.38)    (.86)
                                                              ---------------------------------------------
          Total Distributions                                   (1.47)    (3.12)   (1.74)   (1.84)   (1.30)
- -----------------------------------------------------------------------------------------------------------
NET ASSET VALUE, END OF YEAR                                    $16.91    $16.34   $19.55   $16.99   $15.55
===========================================================================================================
TOTAL RETURN                                                    13.74%    -0.78%   27.04%   23.16%   17.80%
===========================================================================================================
RATIOS/SUPPLEMENTAL DATA
     Net Assets, End of Year (Millions)                       $16,824    $18,355  $20,678  $15,841  $13,008
     Ratio of Total Expenses to Average Net Assets              0.28%      0.27%    0.27%    0.31%    0.45%
     Ratio of Net Investment Income to Average Net Assets       1.56%      1.31%    1.89%    2.75%    3.01%
     Portfolio Turnover Rate                                      56%        48%      61%      34%      32%
===========================================================================================================
</TABLE>
                                       20
<PAGE>
NOTES TO FINANCIAL STATEMENTS
Vanguard Windsor Fund is registered under the Investment  Company Act of 1940 as
a diversified open-end investment company, or mutual fund.

A. The following  significant  accounting policies conform to generally accepted
accounting  principles  for mutual  funds.  The fund  consistently  follows such
policies in preparing its financial statements.
     1. SECURITY  VALUATION:  Equity  securities are valued at the latest quoted
sales  prices  as of the  close  of  trading  on the  New  York  Stock  Exchange
(generally  4:00 p.m.  Eastern time) on the valuation  date; such securities not
traded on the valuation date are valued at the mean of the latest quoted bid and
asked  prices.  Prices are taken from the primary  market in which each security
trades.  Temporary cash investments acquired over 60 days to maturity are valued
using the latest bid prices or using  valuations based on a matrix system (which
considers such factors as security  prices,  yields,  maturities,  and ratings),
both  as  furnished  by  independent  pricing  services.  Other  temporary  cash
investments  are valued at amortized  cost,  which  approximates  market  value.
Securities for which market  quotations are not readily  available are valued by
methods deemed by the Board of Trustees to represent fair value.
     2.  FEDERAL  INCOME  TAXES:  The fund  intends to  continue to qualify as a
regulated   investment  company  and  distribute  all  of  its  taxable  income.
Accordingly,  no provision for federal income taxes is required in the financial
statements.
     3.  REPURCHASE  AGREEMENTS:  The fund,  along  with  other  members  of The
Vanguard  Group,  transfers  uninvested  cash balances to a Pooled Cash Account,
which  is  invested  in  repurchase   agreements  secured  by  U.S.   government
securities.  Securities pledged as collateral for repurchase agreements are held
by a custodian bank until the agreements  mature.  Each agreement  requires that
the market value of the  collateral be sufficient to cover  payments of interest
and principal; however, in the event of default or bankruptcy by the other party
to  the  agreement,  retention  of  the  collateral  may  be  subject  to  legal
proceedings.
     4. FUTURES  CONTRACTS:  The fund uses S&P 500 Index futures  contracts to a
limited  extent,  with the objective of  maintaining  full exposure to the stock
market  while  maintaining  liquidity.  The fund may  purchase  or sell  futures
contracts  to achieve a desired  level of  investment,  whether  to  accommodate
portfolio  turnover or cash flows from capital share  transactions.  The primary
risks  associated  with the use of futures  contracts are imperfect  correlation
between  changes in market  values of stocks  held by the fund and the prices of
futures contracts, and the possibility of an illiquid market.
     Futures contracts are valued at their quoted daily settlement  prices.  The
aggregate  principal  amounts of the contracts are not recorded in the financial
statements.  Fluctuations  in the value of the  contracts  are  recorded  in the
Statement  of Net  Assets  as an  asset  (liability)  and in  the  Statement  of
Operations as  unrealized  appreciation  (depreciation)  until the contracts are
closed, when they are recorded as realized futures gains (losses).
     5.  DISTRIBUTIONS:  Distributions  to  shareholders  are  recorded  on  the
ex-dividend  date.  Distributions  are  determined on a tax basis and may differ
from net investment  income and realized  capital gains for financial  reporting
purposes.
     6. OTHER:  Dividend  income is recorded on the ex-dividend  date.  Security
transactions  are accounted for on the date securities are bought or sold. Costs
used to determine  realized gains (losses) on the sale of investment  securities
are those of the specific securities sold.

B.  Wellington  Management  Company,  LLP,  and as of June 1,  1999,  Sanford C.
Bernstein & Co., Inc., provide investment advisory services to the fund for fees
calculated at an annual percentage rate of average net assets.  The basic fee of
Wellington Management Company, LLP, is subject to quarterly adjustments based on
performance relative to the S&P 500 Index for the preceding three years. For the
year ended October 31, 1999, the aggregate  investment  advisory fee represented
an effective  annual basic rate of 0.12% of the fund's average net assets before
a decrease of $14,040,000 (0.08%) based on performance.
     The  Vanguard  Group  manages  the cash  reserves of the fund on an at-cost
basis.

                                       21
<PAGE>
NOTES TO FINANCIAL STATEMENTS (CONTINUED)

C. The Vanguard Group  furnishes at cost corporate  management,  administrative,
marketing,  and distribution  services. The costs of such services are allocated
to the fund  under  methods  approved  by the  Board of  Trustees.  The fund has
committed to provide up to 0.40% of its net assets in capital  contributions  to
Vanguard. At October 31, 1999, the fund had contributed capital of $3,551,000 to
Vanguard  (included in Other Assets),  representing 0.02% of net assets and 3.5%
of  Vanguard's  capitalization.  The  fund's  Trustees  and  officers  are  also
Directors and officers of Vanguard.
     Vanguard  has asked  the  fund's  investment  advisers  to  direct  certain
security trades,  subject to obtaining the best price and execution,  to brokers
who have agreed to rebate to the fund part of the  commissions  generated.  Such
rebates  are used  solely to reduce the  fund's  management  and  administrative
expenses.  For the year ended October 31, 1999, these  arrangements  reduced the
fund's expenses by $2,460,000 (an annual rate of 0.01% of average net assets).

D. During the year ended October 31, 1999, the fund purchased  $9,799,245,000 of
investment securities and sold $13,843,338,000 of investment  securities,  other
than temporary cash investments.
     During the year ended October 31, 1999,  the fund realized  $81,929,000  of
net capital gains  resulting  from in-kind  redemptions--in  which  shareholders
exchanged  fund  shares for  securities  held by the fund  rather than for cash.
Because  such gains are not  taxable  to the fund,  and are not  distributed  to
shareholders, they have been reclassified from accumulated net realized gains to
paid in capital.

E. At October 31, 1999, net unrealized appreciation of investment securities for
financial   reporting  and  federal  income  tax  purposes  was  $2,063,119,000,
consisting of unrealized gains of $3,767,787,000 on securities that had risen in
value since their purchase and $1,704,668,000 in unrealized losses on securities
that had fallen in value since their purchase.
     At  October  31,  1999,  the  aggregate  settlement  value of open  futures
contracts  expiring in December  1999 and the  related  unrealized  appreciation
were:
- --------------------------------------------------------------------------------
                                                            (000)
                                            ------------------------------------
                                                AGGREGATE
                            NUMBER OF          SETTLEMENT            UNREALIZED
FUTURES CONTRACTS         LONG CONTRACTS          VALUE             APPRECIATION
- --------------------------------------------------------------------------------
S&P 500 Index                  359              $123,514              $6,015
S&P MidCap 400 Index           130                26,081                 253
- --------------------------------------------------------------------------------
Unrealized appreciation of $6,268,000 on open future contracts is required to be
treated as realized gain for tax purposes.

F. The market value of securities on loan to broker/dealers at October 31, 1999,
was  $29,871,000,  for which the fund held cash collateral of $30,270,000.  Cash
collateral received is invested in repurchase agreements.

                                       22
<PAGE>
REPORT OF INDEPENDENT ACCOUNTANTS

To the Shareholders and Trustees of
Vanguard Windsor Fund

In our  opinion,  the  accompanying  statement  of net  assets  and the  related
statements  of  operations  and of  changes  in net  assets  and  the  financial
highlights present fairly, in all material  respects,  the financial position of
Vanguard  Windsor  Fund (the  "Fund") at October  31,  1999,  the results of its
operations  for the year then  ended,  the changes in its net assets for each of
the two years in the period then ended and the financial  highlights for each of
the five years in the period then ended, in conformity  with generally  accepted
accounting  principles.  These  financial  statements  and financial  highlights
(hereafter referred to as "financial  statements") are the responsibility of the
Fund's  management;  our  responsibility  is to  express  an  opinion  on  these
financial  statements  based on our  audits.  We  conducted  our audits of these
financial  statements in accordance with generally  accepted auditing  standards
which require that we plan and perform the audit to obtain reasonable  assurance
about whether the financial  statements  are free of material  misstatement.  An
audit includes examining,  on a test basis,  evidence supporting the amounts and
disclosures in the financial  statements,  assessing the  accounting  principles
used and  significant  estimates made by management,  and evaluating the overall
financial  statement  presentation.  We believe that our audits,  which included
confirmation  of  securities  at October  31,  1999 by  correspondence  with the
custodian  and  brokers,  provide a reasonable  basis for the opinion  expressed
above.

PricewaterhouseCoopers LLP

Thirty South Seventeenth Street
Philadelphia, Pennsylvania 19103

November 30, 1999

                                       23
<PAGE>
- --------------------------------------------------------------------------------
SPECIAL 1999 TAX INFORMATION (UNAUDITED) FOR
VANGUARD WINDSOR FUND

This  information  for the fiscal  year ended  October  31,  1999,  is  included
pursuant to provisions of the Internal Revenue Code.
     The fund  distributed  $1,341,486,000  as capital gain dividends  (from net
long-term  capital  gains) to  shareholders  in December  1998,  all of which is
designated as a 20% rate gain distribution. For corporate shareholders, 32.4% of
investment  income (dividend income plus short-term gains, if any) qualifies for
the dividends-received deduction.
- --------------------------------------------------------------------------------
                                       24
<PAGE>
- --------------------------------------------------------------------------------
THE PEOPLE WHO GOVERN YOUR FUND
The  Trustees of your mutual fund are there to see that the fund is operated and
managed in your best interests  since,  as a shareholder,  you are part owner of
the fund.  Your  fund  Trustees  also  serve on the  Board of  Directors  of The
Vanguard  Group,  which is owned by the  funds  and  exists  solely  to  provide
services to them on an at-cost basis.
     Seven of Vanguard's nine board members are  independent,  meaning that they
have no  affiliation  with  Vanguard or the funds they  oversee,  apart from the
sizable personal investments they have made as private  individuals.  They bring
distinguished  backgrounds  in business,  academia,  and public service to their
task of working with Vanguard officers to establish the policies and oversee the
activities of the funds.
     Among board members' responsibilities are selecting investment advisers for
the  funds;  monitoring  fund  operations,  performance,  and  costs;  reviewing
contracts;  nominating  and  selecting  new  Trustees/Directors;   and  electing
Vanguard officers.
     The list below provides a brief description of each Trustee's  professional
affiliations.  Noted in  parentheses is the year in which the Trustee joined the
Vanguard Board.

TRUSTEES
JOHN  C.  BOGLE  o  (1967)   Founder,   Senior   Chairman  of  the  Board,   and
Director/Trustee  of The  Vanguard  Group,  Inc.,  and  each  of the  investment
companies in The Vanguard Group.

JOHN J. BRENNAN o (1987)  Chairman of the Board,  Chief Executive  Officer,  and
Director/Trustee  of The  Vanguard  Group,  Inc.,  and  each  of the  investment
companies in The Vanguard Group.

JOANN HEFFERNAN HEISEN o (1998) Vice President, Chief Information Officer, and a
member of the  Executive  Committee of Johnson & Johnson;  Director of Johnson &
JohnsonoMerck Consumer Pharmaceuticals Co., The Medical Center at Princeton, and
Women's Research and Education Institute.

BRUCE K.  MACLAURY o (1990)  President  Emeritus of The  Brookings  Institution;
Director of  American  Express  Bank Ltd.,  The St. Paul  Companies,  Inc.,  and
National Steel Corp.

BURTON G. MALKIEL o (1977)  Chemical  Bank  Chairman's  Professor of  Economics,
Princeton  University;  Director of Prudential  Insurance Co. of America,  Banco
Bilbao Gestinova,  Baker Fentress & Co., The Jeffrey Co., and Select Sector SPDR
Trust.

ALFRED M. RANKIN, JR. o (1993) Chairman,  President, and Chief Executive Officer
of NACCO Industries, Inc.; Director of NACCO Industries, The BFGoodrich Co., and
The Standard Products Co.

JOHN C. SAWHILL o (1991)  President  and Chief  Executive  Officer of The Nature
Conservancy;  formerly,  Director  and  Senior  Partner  of  McKinsey  & Co. and
President  of New York  University;  Director of Pacific Gas and  Electric  Co.,
Procter & Gamble Co., NACCO Industries, and Newfield Exploration Co.

JAMES O. WELCH, JR. o (1971) Retired Chairman of Nabisco Brands,  Inc.;  retired
Vice Chairman and Director of RJR Nabisco;  Director of TECO Energy,  Inc.,  and
Kmart Corp.

J. LAWRENCE  WILSON o (1985)  Retired  Chairman of Rohm & Haas Co.;  Director of
Cummins Engine Co. and The Mead Corp.; Trustee of Vanderbilt University.
- --------------------------------------------------------------------------------
OTHER FUND OFFICERS

RAYMOND J. KLAPINSKY o Secretary; Managing
Director and Secretary of The Vanguard  Group,
Inc.;  Secretary  of each of the  investment companies
in The Vanguard Group.

THOMAS J. HIGGINS o Treasurer; Principal of The
Vanguard Group, Inc.; Treasurer of each of the
investment companies in The Vanguard Group.

VANGUARD MANAGING DIRECTORS
R. GREGORY BARTON o Legal Department.
ROBERT A. DISTEFANO o Information Technology.
JAMES H. GATELY o Individual Investor Group.
KATHLEEN C. GUBANICH o Human Resources.
IAN A. MACKINNON o Fixed Income Group.
F. WILLIAM MCNABB, III o Institutional Investor Group.
MICHAEL S. MILLER o Planning and Development.
RALPH K. PACKARD o Chief Financial Officer.
GEORGE U. SAUTER o Core Management Group.
<PAGE>
ABOUT OUR COVER
Our cover art,  depicting HMS Vanguard at sea, is a
reproduction  of Leading the Way, a 1984 work created
and  copyrighted by noted naval artist Tom Freeman,
of Forest Hill, Maryland.

All comparative mutual fund data are from Lipper Inc. or Morningstar,
Inc., unless otherwise noted.

"Standard & Poor's(R),"  "S&P(R),"  "S&P  500(R),"  "Standard & Poor's 500,"
and "500" are trademarks of The McGraw-Hill Companies, Inc.

Frank Russell Company is the owner of trademarks and copyrights
relating to the Russell Indexes.  "Wilshire 4500" and "Wilshire 5000"
are trademarks of Wilshire Associates.

[SHIP LOGO]
[THE VANGUARD GROUP(R) LOGO]
Post Office Box 2600
Valley Forge, Pennsylvania 19482-2600

WORLD WIDE WEB
www.vanguard.com

FUND INFORMATION
1-800-662-7447

INDIVIDUAL ACCOUNT SERVICES
1-800-662-2739

INSTITUTIONAL INVESTOR SERVICES
1-800-523-1036

This report is intended for the fund's
shareholders.  It may not be distributed
to  prospective  investors  unless it
is preceded or  accompanied by the
current fund prospectus.

Q220-12/09/1999

(C) 1999 The Vanguard Group, Inc.
All rights reserved.
Vanguard Marketing
Corporation, Distributor.
<PAGE>

VANGUARD(R)
WINDSOR II
FUND

Annual Report
October 31, 1999

[SHIP GRAPHIC]
[A MEMBER OF THE VANGUARD GROUP LOGO]
<PAGE>
[PHOTO OF JOHN C. BOGLE]
JOHN C. BOGLE

FELLOW SHAREHOLDERS:

     TWO ROADS  DIVERGED IN A WOOD,  AND I--I TOOK THE ONE LESS TRAVELED BY, AND
     THAT HAS MADE ALL THE DIFFERENCE.

I can think of no better  words than those of Robert Frost to begin this special
letter to our shareholders,  who have placed such extraordinary  trust in me and
in Vanguard  over the past quarter  century.  When the firm was founded 25 years
ago,  we  deliberately  took a new road to  managing a mutual  fund  enterprise.
Instead of having the funds controlled by an outside management company with its
own  financial  interests,  the  Vanguard  funds--there  were  only  11 of  them
then--would be controlled by their own  shareholders and operate solely in their
financial interests.  The outcome of our unprecedented  decision was by no means
certain. We described it then as "The Vanguard Experiment."
     Well, I guess it's fair to say it's an experiment no more.  During the past
25 years,  the assets we hold in  stewardship  for investors  have grown from $1
billion  to more  than  $500  billion,  and I believe  that our  reputation  for
integrity,  fair-dealing,  and sound investment  principles is second to none in
this  industry.  Our  staggering  growth--which  I  never  sought--has  come  in
important part as a result of the simple investment ideas and basic human values
that are the foundation of my personal philosophy.  I have every confidence that
they  will  long  endure at  Vanguard,  for they are the  right  ideas and right
values, unshakable and eternal.
     While Emerson believed that "an institution is the lengthened shadow of one
man," Vanguard today is far greater than any  individual.  The Vanguard crew has
splendidly  implemented  and  enthusiastically  supported our founding ideas and
values, and deserves the credit for a vital role in forging our success over the
years.  It is a  dedicated  crew of fine human  beings,  working  together in an
organization  that is well prepared to press on regardless long after I am gone.
Creating and leading this  enterprise has been an exhilarating  run.  Through it
all,  I've taken the kudos and the blows  alike,  enjoying  every  moment to the
fullest,  and even getting a second chance at life with a heart transplant three
years ago. What more could a man ask?
     While I shall no longer be serving on the Vanguard  Board, I want to assure
you that I will remain  vigorous and active in a newly  created  Vanguard  unit,
researching the financial markets, writing, and speaking. I'll continue to focus
whatever  intellectual  power and  ethical  strength  I possess on my mission to
assure that mutual fund investors everywhere receive a fair shake. In the spirit
of Robert Frost:

     BUT I HAVE PROMISES TO KEEP,  AND MILES TO GO BEFORE I SLEEP,  AND MILES TO
GO BEFORE I SLEEP.

     You have given me your loyalty and friendship over these long years,  and I
deeply  appreciate  your  thousands  of letters of support.  For my part, I will
continue to keep an eagle eye on your  interests,  for you deserve no less.  May
God bless you all, always.
- --------------------------------------------------------------------------------
CONTENTS
REPORT FROM THE CHAIRMAN ........... 1    FUND PROFILE .......................10
AFTER-TAX RETURNS REPORT ........... 5    PERFORMANCE SUMMARY ................12
THE MARKETS IN PERSPECTIVE ......... 6    FINANCIAL STATEMENTS ...............13
ADVISER'S REPORT ................... 8    REPORT OF INDEPENDENT ACCOUNTANTS ..22
- --------------------------------------------------------------------------------
<PAGE>
[PHOTO OF JOHN J. BRENNAN]
JOHN J. BRENNAN

REPORT FROM THE CHAIRMAN
Vanguard  Windsor  II Fund made a poor  showing  during  its 1999  fiscal  year,
returning  4.6% during the 12 months  ended  October 31, when broad stock market
measures advanced nearly 26%.
     The table at right presents the fiscal-year  total returns  (capital change
plus   reinvested   dividends)   for  the   Windsor   II   Fund,   the   average
large-capitalization  value mutual fund,  the unmanaged  S&P 500 Index,  and the
value stock  component of the S&P 500. As you can see,  your fund's return was a
full 13  percentage  points  behind that of its average  peer,  and more than 21
percentage  points  behind that of the S&P 500 Index,  which was  propelled by a
roaring  market  for large  technology  stocks.  Windsor  II's  return  was 14.4
percentage points behind the return of the S&P 500/BARRA Value Index, which is a
good measure of the types of stocks that Windsor II emphasizes.  It was, by far,
the fund's worst  performance  ever relative to the S&P 500 Index and to the S&P
500/BARRA Value Index.
- --------------------------------------------
                            TOTAL RETURNS
                          FISCAL YEAR ENDED
                           OCTOBER 31, 1999
- --------------------------------------------
Vanguard Windsor II Fund         4.6%
- --------------------------------------------
Average Large-Cap Value Fund*   17.6%
- --------------------------------------------
S&P 500 Index                   25.7%
- --------------------------------------------
S&P 500/BARRA Value Index       19.0%
- --------------------------------------------
*Derived from data provided by Lipper Inc.

     The fund's total return is based on net asset values of $31.07 per share on
October 31, 1998,  and $29.03 per share on October 31, 1999, and is adjusted for
dividends  totaling  $0.74  per  share  paid from net  investment  income  and a
distribution  of $2.67  per share  paid  from net  realized  capital  gains.  We
estimate that the fund will make a distribution of approximately  $2.40 from net
realized capital gains in December 1999.

FINANCIAL MARKETS IN REVIEW
The fiscal year ended October 31 comprised two distinctly  different halves. For
most of the first half, stock prices  worldwide were rebounding  strongly from a
slump in the summer of 1998 that had been  prompted by economic  crises in Asia,
Russia,  and parts of Latin America.  The stock market's comeback was aided by a
pickup in global  economic  activity  and by  interest  rate  reductions  by the
Federal  Reserve  Board  that  autumn.  These  developments--and  the  continued
ebullience of the U.S. economy--erased investors' fears that the troubles abroad
would depress business  activity and profits at home. Even though interest rates
rose during the six months from October 31 through  April 30, the stock  market,
as measured by the Wilshire  5000 Total Market  Index,  gained 22.8% and the S&P
500 Index was up 22.3%.  The  returns of value  stocks and  growth  stocks  were
nearly  identical  during the six months,  with the S&P 500's  growth  component
returning 22.6% and its value component earning 21.7%.
     However,  during the  second  half of our fiscal  year,  most stock  prices
stagnated  or fell  (with the  notable  exception  of  technology  stocks).  The
Wilshire 5000 advanced  2.3%,  bringing its full-year  return to 25.7%.  The S&P
500's second-half return of 2.7% brought it to an identical 25.7% return for our
fiscal year. The second half was particularly tough on large value stocks, which
returned -2.2% from May through October, compared with a 7.3% return for the S&P
500's growth stocks. Large-cap growth stocks were the strongest

                                       1
<PAGE>
market  sector  during the fiscal  year,  led by simply  stupendous  gains for a
number of technology stocks,  such as QUALCOMM (700%), Sun Microsystems  (263%),
Cisco Systems (135%), Microsoft (75%), and Intel (74%). The growth stocks within
the S&P 500 Index gained 31.6%, while the index's value stocks returned 19.0%.
     One factor  restraining the stock market in general was a strong uptrend in
interest rates starting in February.  The Federal Reserve  encouraged this move,
acting in late June and again in August to boost short-term  interest rates by a
total of 0.5 percentage point.  Fears of a global economic slump were supplanted
by worries that economic  growth--especially in the United States--was so strong
that it would cause wages and commodity prices to surge, pushing up inflation.
     For  the  full  year,   yields  on  long-term  U.S.   Treasury  bonds  rose
significantly.  The yield of the 30-year Treasury increased exactly 1 percentage
point (100 basis points) to 6.16% on October 31, 1999.  Bond prices,  which move
in the opposite  direction from interest rates, fell during the year. The Lehman
Brothers  Aggregate Bond Index, a benchmark for taxable bonds, eked out a return
of 0.5% for the year,  as its interest  income of 6.2% only barely  offset price
declines of -5.7%.

FISCAL 1999 PERFORMANCE OVERVIEW
Vanguard  Windsor II Fund's  4.6% total  return  during the 1999 fiscal year was
mediocre on an absolute basis and even worse relative to competing  mutual funds
and market indexes.
     The fund got off to a relatively  strong start,  returning  6.5% during the
first two months of the period and 17.3% for the first half of the fiscal  year.
But the second half was a different,  and very  disappointing,  story.  The fund
posted a negative  total return of -10.8% from May through  October,  well below
the 2.7% return of the S&P 500 Index,  and the -2.2% return of the S&P 500/BARRA
Value  Index,  which is a better  measure of the types of stocks that Windsor II
emphasizes.
     Though the  market's  tilt toward  growth  stocks  over value  stocks was a
detriment  to your fund  during the  period,  our  difficulties  went far beyond
investment  style.  Even when  compared  specifically  to the Value  Index,  our
performance was disappointing.  Our return was 14.4 percentage points lower than
the 19.0%  return of the index.  As a value  fund,  Windsor II focuses on stocks
that are relatively cheap in terms of measures such as price/earnings ratios and
book value and that pay dividend yields  considerably  above the market average.
This  mandate   naturally  steered  the  fund  toward  certain  market  segments
(financial services and utilities) and away from others, particularly technology
stocks,  which  at  present  carry  sky-high  valuations  and pay  little  or no
dividends.  On a relative  basis,  our small  commitment  to the  top-performing
technology  sector (about 4% of our average  assets,  versus 18% for the S&P 500
Index) meant big trouble for the fund, given the sector's return of 67%. Our big
stake in the financial-services group (26% of average assets for Windsor II; 16%
for the index) was also troublesome because of the relatively low returns earned
by many bank stocks during the period.
     The bulk of our shortfall,  however,  stemmed from the inferior performance
of stocks selected by our investment advisers,  particularly among issues in the
consumer-discretionary   group  and  the  utilities  sector.   As  always,   the
performances of the stocks selected by each of our four advisers varied from the
others  during fiscal 1999.  The prices of many of the stocks we  own--including
some of our biggest  holdings--declined  sharply  during the fiscal year because
the market had expected better  earnings.  Waste Management Inc., one of our ten
largest holdings six months ago, was hit especially hard. The


                                       2
<PAGE>
company's share price plummeted about 70% during the period--much of that during
a brief span this fall--in  response to the  revelation of accounting  problems,
losses,  and the departure of its chairman.  Other big names that suffered sharp
drops included Xerox,  Service Corporation  International,  and J.C. Penney. The
Adviser's Report beginning on page 8 provides further details.
     While none of us on the  Windsor II team is happy with our  results for the
fiscal year, our belief in the fund's value-oriented  investment strategy is not
shaken.  Since its  inception  in June 1985,  Windsor II has enjoyed  periods of
outperformance  (it topped the S&P 500 Index from  fiscal  1991  through  fiscal
1993) as well as  underperformance  (it  trailed  large-cap  stocks  in 1997 and
1998). These variations from the broad market are the nature of active portfolio
management  and the fund's  emphasis on  out-of-favor  stocks.  The challenge of
active  management,  naturally,  is to make those  variations  positive.  We are
closely  monitoring the portfolio,  and we remain  confident in the abilities of
the four  investment  advisers who select stocks for Windsor II. We fully expect
the fund to provide competitive returns over the long run.

- --------------------------------------------------------------------------------
                                                           TOTAL ASSETS MANAGED
                                                          AS OF OCTOBER 31, 1999
                                                        ------------------------
                                                        $ MILLION     PERCENTAGE
- --------------------------------------------------------------------------------
Barrow, Hanley, Mewhinney & Strauss, Inc.                 $19,733            64%
Equinox Capital Management, Inc.                            4,135            14
Tukman Capital Management, Inc.                             3,716            12
Vanguard Core Management Group                              1,781             6
Cash Reserve*                                               1,176             4
- --------------------------------------------------------------------------------
Total                                                     $30,541           100%
- --------------------------------------------------------------------------------
*    This  cash  reserve  is  invested  in  equity  index  futures  to  simulate
     investment in stocks; each adviser may also maintain a modest cash reserve.

     The table above shows the share of assets supervised by each adviser at the
end of the fiscal year.

LONG-TERM PERFORMANCE OVERVIEW
Any annual review of a mutual fund's  performance  should also include a look at
the fund's  longer-term  record.  The table below  presents  the average  annual
returns of the Windsor II Fund and its  comparative  benchmarks for the past ten
years. It also presents the results of hypothetical  $10,000  investments made a
decade ago in the fund, its average  competitor,  the S&P 500 Index, and the S&P
500/BARRA Value Index.
- --------------------------------------------------------------------------------
                                                         TOTAL RETURNS
                                                10 YEARS ENDED OCTOBER 31, 1999
                                             -----------------------------------
                                             AVERAGE             FINAL VALUE OF
                                              ANNUAL               A $10,000
                                              RATE            INITIAL INVESTMENT
- --------------------------------------------------------------------------------
Vanguard Windsor II Fund                      14.5%                $38,787
- --------------------------------------------------------------------------------
Average Large-Cap Value Fund                  15.2%                $41,026
- --------------------------------------------------------------------------------
S&P 500 Index                                 17.8%                $51,526
- --------------------------------------------------------------------------------
S&P 500/BARRA Value Index                     15.4%                $41,790
- --------------------------------------------------------------------------------
     As you might expect,  your fund's poor  performance over the past 12 months
had a considerable  negative impact on its longer-term results. One year ago--at
the end of the 1998 fiscal  year--Windsor  II's average  annual  return over the
previous decade was 1.8 percentage  points better than that of its average peer.
Now, just 12 months later,  our annualized  return over the past ten years comes
up short by 0.7 percentage  point.  A $10,000  investment in the Windsor II Fund
would  have  grown  to  $38,787,  compared  with the  $41,026  that  would  have
accumulated in the average  large-cap value fund over the same period.

                                       3
<PAGE>
A  similar  investment  in the  large-cap-dominated  S&P 500  Index  would  have
amounted to  $51,526,  a  terrific--and  I'd say  unsustainable--average  annual
return of 17.8%.
     Our ultimate goal, of course, is to provide performance that is superior to
that of  comparable  mutual  funds  over  long  periods.  We are  aided  in this
objective  by our  low  expenses,  which  provide  us  with  an  advantage  over
higher-cost  funds.  Our expense ratio  (expenses as a percentage of average net
assets) is 0.37%, nearly a full percentage point lower than the 1.26% charged by
the average peer mutual fund.  Our low costs may provide little comfort during a
period when our  performance  lags,  but rest assured  that this cost  advantage
remains a powerful ally in our quest to provide superior long-term returns.
     The returns earned by  stocks--particularly  large growth  stocks--over the
past decade were high by historical  standards and will probably be lower in the
future. This is not a prediction, but rather a prudent assumption that should be
a part of every investor's long-range investment planning. The long-term average
return for stocks is about 11%, but that average  includes lean years as well as
the fabulous decade of the 1990s.

IN SUMMARY
Though the U.S. stock market was rewarding as a whole during the past 12 months,
the narrow nature of the market's gains  highlighted  the fact that investing in
stocks is a risky endeavor.  Individual stocks, and even entire industry groups,
move in different directions at different times and in varying degrees,  just as
the returns of stocks, bonds, and short-term  investments diverge and fluctuate.
That is why building and maintaining an investment  program that has exposure to
the  different  asset  classes,  as well as to a variety of issues  within  each
class,  is the surest  road to  long-term  investing  success.  Creating  such a
program tailored to your objectives,  time horizon for investing,  and tolerance
for risk--and  sticking with it through good times and bad--is a sound  approach
to  participating  in the rewards of the financial  markets  while  limiting the
risk.

/S/
John J. Brennan
Chairman and Chief Executive Officer

November 12, 1999
================================================================================
A NOTE OF THANKS TO OUR FOUNDER
================================================================================
As you may have read on the inside  cover of our report,  our  founder,  John C.
Bogle,  is retiring  December  31, 1999,  as Senior  Chairman of our Board after
nearly 25 years of devoted  service to Vanguard and our  shareholders.  Vanguard
investors  have Jack to thank for  creating a truly  mutual  mutual fund company
that operates solely in the interest of its fund  shareholders.  And mutual fund
investors  everywhere have benefited from his energetic  efforts to improve this
industry.  Finally, on a personal note, I am forever grateful to Jack for giving
me the opportunity to join this great company in 1982.

                                       4
<PAGE>
A REPORT ON YOUR FUND'S AFTER-TAX RETURNS
Beginning  with this annual  report,  Vanguard is pleased to provide a review of
the  Windsor  II  Fund's  after-tax  performance.   The  figures  on  this  page
demonstrate  the  considerable  impact that  federal  income taxes can have on a
fund's return--an important  consideration for investors who own mutual funds in
taxable  accounts.  While the pretax return is most often used to tally a fund's
performance,   the  fund's  after-tax  return,   which  accounts  for  taxes  on
distributions of capital gains and income dividends,  is a better representation
of the return that many investors actually  received.  IF YOU OWN THE WINDSOR II
FUND IN A  TAX-DEFERRED  ACCOUNT SUCH AS AN INDIVIDUAL  RETIREMENT  ACCOUNT OR A
401(K), THIS INFORMATION DOES NOT APPLY TO YOU. SUCH ACCOUNTS ARE NOT SUBJECT TO
CURRENT TAXES.
     The table below presents the pretax and after-tax returns for your fund and
an appropriate peer group of mutual funds. Two things to keep in mind:
     o The after-tax return calculations use the top federal income tax rates in
effect at the time of each  distribution.  The tax burden,  therefore,  would be
somewhat  less, and the after-tax  return  somewhat more, for those in lower tax
brackets.
     o The peer funds' returns are provided by Morningstar,  Inc.  (Elsewhere in
this report,  returns for comparable mutual funds are derived from data provided
by Lipper Inc., which differs somewhat.)
- --------------------------------------------------------------------------------
                               AVERAGE ANNUAL RETURNS: PRETAX AND AFTER-TAX
                                       PERIODS ENDED OCTOBER 31, 1999
                           -----------------------------------------------------
                               1 YEAR            5 YEARS           10 YEARS
                           ----------------  ----------------  -----------------
                           PRETAX AFTER-TAX  PRETAX AFTER-TAX  PRETAX AFTER-TAX
- --------------------------------------------------------------------------------
Vanguard Windsor II Fund     4.6%    1.6%     20.1%   17.3%     14.5%    11.9%
Average Large Value Fund*   12.2    10.3      18.2    15.3      14.0     11.4
- --------------------------------------------------------------------------------
*Based on data from Morningstar, Inc.

     As you can see,  the Windsor II Fund's  pretax total return of 4.6% for the
12 months ended October 31, 1999,  was reduced by taxes to 1.6%. In other words,
for investors in the highest tax bracket,  the fund's pretax return was cut by 3
percentage  points. In comparison,  the average  comparable fund earned a pretax
return of 12.2% and an after-tax return of 10.3%, a difference of 1.9 percentage
points.
     Over longer periods, the fund has fared better. Over the five- and ten-year
periods ended October 31, 1999, our fund generated  slightly higher returns than
the peer-group average, both before and after taxes.
     We stress that because many interrelated  factors affect how tax-friendly a
fund may be,  it's very  difficult  to  predict  tax  efficiency.  A fund's  tax
efficiency  can be influenced by its turnover  rate,  the types of securities it
holds,  the accounting  practices it uses when selling shares,  and the net cash
flow it receives.
     Finally, it's important to understand that our calculation does not reflect
the tax effect of your own investment  activities.  Specifically,  you may incur
additional capital gains  taxes--thereby  lowering your after-tax return--if you
decide to sell all or some of your shares.

A  NOTE  ABOUT  OUR   CALCULATIONS:   Pretax  total  returns   assume  that  all
distributions   received  (income  dividends,   short-term  capital  gains,  and
long-term  capital  gains) are  reinvested  in new shares,  while our  after-tax
returns assume that  distributions  are reduced by any taxes owed on them before
reinvestment.  When  calculating  the taxes due, we used the highest  individual
federal  income  tax  rates at the time of the  distributions.  Those  rates are
currently 39.6% for dividends and short-term capital gains and 20% for long-term
capital gains. State and local income taxes were not considered. The competitive
group returns provided by Morningstar are calculated in a manner consistent with
that used for Vanguard funds.
                                       5
<PAGE>
THE MARKETS IN PERSPECTIVE
YEAR ENDED OCTOBER 31, 1999

Caution  followed  exuberance  in the U.S.  stock market  during the fiscal year
ended October 31, 1999.  Improving economic  conditions during the first half of
the year set off a raucous  rally from the lows of summer 1998,  when fears of a
global  economic slump swept world markets.  However,  during the second half of
the fiscal  year,  interest  rates kept  rising,  pulling  down bond  prices and
tempering the stock market's optimism. The notion of a global slump was replaced
by worries  that  economic  growth  might be so strong as to threaten a surge in
inflation.

U.S. STOCK MARKETS
A booming U.S. economy and solid increases in corporate earnings lifted the U.S.
stock market,  especially during the first half of the fiscal year. The nation's
economic output increased by about 4% during the year. Consumer spending,  which
accounts for roughly  two-thirds of economic  activity,  powered the  expansion.
Americans spent virtually every dollar they earned,  encouraged by rising wealth
from a long bull market,  plentiful employment,  and rising incomes.  (After-tax
personal  income rose about 5% during the year;  unemployment  fell to a 30-year
low of 4.1% of the workforce in October.)
- --------------------------------------------------------------------------------
                                                      AVERAGE ANNUAL RETURNS
                                                  PERIODS ENDED OCTOBER 31, 1999
                                                  ------------------------------
                                                      1 YEAR   3 YEARS   5 YEARS
- --------------------------------------------------------------------------------
STOCKS
 S&P 500 Index                                         25.7%     26.5%     26.0%
 Russell 2000 Index                                    14.9       9.4      12.6
 Wilshire 5000 Index                                   25.7      23.8      23.8
 MSCI EAFE Index                                       23.4      12.5       9.5
- --------------------------------------------------------------------------------
BONDS
 Lehman Aggregate Bond Index                            0.5%      6.2%      7.9%
 Lehman 10 Year Municipal Bond Index -1.2               5.2       7.0
 Salomon Smith Barney 3-Month U.S. Treasury Bill Index  4.6       5.0       5.2
- --------------------------------------------------------------------------------
OTHER
 Consumer Price Index                                   2.6%      2.0%      2.4%
- --------------------------------------------------------------------------------
     From October 31, 1998, through April 30, 1999, the stock market rose 22.8%,
as  measured by the  Wilshire  5000 Total  Market  Index.  Investor  confidence,
already  high due to the  booming  economy,  was  bolstered  by easier  monetary
policy--the  Federal Reserve cut short-term  interest rates in November 1998 for
the third time in less than two months.  But by summer, the Fed reversed course,
twice boosting its target for short-term  interest rates to slow the economy and
reduce inflationary pressures.
     Higher interest rates helped take the steam out of the stock market's rally
during the second half of the fiscal  year,  even though  estimates of corporate
earnings kept rising.  Higher rates tend to hurt stocks  because many  investors
use current interest rates to discount the value of a stock's projected earnings
and dividends. The higher the rate, the more future earnings are discounted, and
the less investors will pay for the stock now. After a second-half gain of 2.3%,
the Wilshire 5000 Index recorded a 25.7% return for the full fiscal year.
     Big stocks  outperformed  small  stocks in fiscal 1999,  and growth  stocks
outpaced   value   stocks.   The  S&P  500   Index,   which  is   dominated   by
large-capitalization  stocks,  gained

                                       6
<PAGE>
25.7%, while the small-cap Russell 2000 Index was up 14.9%. Growth stocks--whose
high prices in relation to earnings,  book value,  and  dividends  indicate high
expectations  for future  growth--lost  none of their  appeal,  despite  soaring
valuations for many. Both large- and small-cap growth issues gained roughly 30%,
while  value  stocks  within  the S&P 500 Index were up 19.0%,  and the  Russell
2000's value stocks had a scant 0.7% return.
     The  growth/value  gap was due  partly  to the  incredible  performance  of
technology stocks, most of which are classified as growth issues. Within the S&P
500 Index, tech stocks gained 67% during the fiscal year.  Advances of about 30%
were  recorded by retailers and other  consumer-discretionary  stocks and by the
utilities sector,  where gains were concentrated in  telecommunications  stocks.
The only sector with a loss was consumer staples (-8%),  where food and beverage
company  stocks  suffered  from falling  profits.Other  laggards were the auto &
transportation sector (+6%) and health-care stocks (+9%).

U.S. BOND MARKETS
Rapid  economic  growth was a help to the stock market but a hindrance to bonds.
Investors  worried that,  with  unemployment so low, growth above the 2.5% to 3%
range would cause wages and prices to accelerate.  Indeed,  inflation did rise a
bit,  although the Consumer  Price Index was up a relatively  modest 2.6% during
the 12-month period.
     As mentioned, the Fed sought to combat inflationary pressures by increasing
short-term  interest rates by a quarter-point on June 30 and again on August 24.
The bond market was already  pushing up rates well before the Fed acted.  Yields
of long-term U.S.  Treasury  bonds began rising  significantly  in February.  By
fiscal  year-end,  the 30-year  Treasury  bond's yield was 6.16%, up precisely 1
percentage point for the year. The 10-year Treasury's yield rose 1.41 percentage
points,  from 4.61% to 6.02%.  Short-term interest rates didn't rise as far, and
3-month Treasury bill yields were up 0.77 point to 5.09% at fiscal year-end.
     Rising  interest  rates mean lower  prices for existing  bonds,  of course.
Price declines were higher for  longer-term  bonds,  which are most sensitive to
changing  rates.  For the  taxable  bond  market as a whole,  as measured by the
Lehman Aggregate Bond Index,  prices fell -5.7%,  resulting in a total return of
just 0.5% for the  fiscal  year.  High-yield  (junk)  bonds and  mortgage-backed
securities posted higher returns than Treasuries.

INTERNATIONAL STOCK MARKETS
International  markets  soared in local  currencies  during the 12 months  ended
October  31,  with  European  stocks  gaining  22.7% and  Pacific-region  stocks
advancing 37.8%. The U.S. dollar rose in value against most European  currencies
but fell  against the  Japanese  yen.  For U.S.  investors,  the upshot of these
currency  fluctuations  was to trim returns from Europe to 12.7% in dollar terms
and to boost returns from the Pacific to 50.5%.
     In the major developed  international markets, U.S. investors earned 23.4%,
as measured by the Morgan Stanley Capital International Europe, Australasia, Far
East (EAFE)  Index.  The bull  markets in most  nations  stemmed  from a renewed
appetite  for  risk on the  part of  investors  encouraged  by  clear  signs  of
expanding business activity and generally easier monetary policy.  Japan and the
rest of Asia, which were hit hardest by currency and economic crises in 1997 and
1998, saw the biggest gains.  In Japan,  massive  government  spending  programs
appeared to be working--at  least in the short run--to lift that nation out of a
recession.
     Emerging  markets,  as measured by the Select Emerging  Markets Free Index,
gained 34.1% for U.S.  investors,  as local  returns of better than 70% were cut
nearly in half by weaker currencies in Latin America and eastern Europe.

                                       7
<PAGE>
ADVISER'S REPORT

We have been writing shareholder letters for a long time, but this is by far the
most difficult.  Vanguard Windsor II Fund declined -10.8% during the second half
of the fiscal year ended October 31, while the S&P 500 Index gained 2.7% and the
S&P 500/BARRA Value Index declined -2.2%.  Results for the full fiscal year were
equally disappointing, with a 4.6% return for the fund versus gains of 25.7% for
the S&P 500 and 19.0% for the Value Index. We are not doing things  differently,
and our holdings have not radically changed, but the stock market surely has.
     The economy  continues to be vigorous,  with  employment high and inflation
reputed to be very low. Despite a benign Consumer Price Index,  prices have been
rising  for  certain  items,  such as  airline  tickets,  hotel  rooms,  energy,
chemicals,  housing,  building  materials,  and health  care.  Plainly,  for the
average  consumer,  increases in such  products  more than offset the decline in
computer  prices.  In a very real way, the stock market has been responsible for
much of the good economic  news--including the federal budget surplus and strong
consumer  spending.  Therefore,  the Federal Reserve follows  equities with more
intense interest than ever before.
     The top 10% of stocks in the Value Index, in terms of their contribution to
its  fiscal-year  return,  account for 41% of the index's market  weight.  Those
companies, on average, sell at 43.5 times next year's estimated earnings and 5.0
times current book value. On average,  they have a 1.1% dividend yield.  Because
we emphasize  stocks with low  price/earnings  ratios (the fund's average P/E is
65% of the  market's),  low price/book  ratios (53% of the  market's),  and high
current yields (twice the  market's),  we did not  participate  much in that top
tenth of the Value  Index.  If we had known how "cheap" they were in the eyes of
the market, this letter would have been easier to write.
     For the past year,  investors  have been  drawn to growth as never  before.
They seemed to feel required to sell, at any price, any stock that fell short of
expectations in revenues or earnings.  Even small  disappointments were punished
by  instantaneous  declines  of  25%  or  more.  Our  problem  issues  of  Waste
Management,  Raytheon, Xerox, Allstate, Service Corporation  International,  and
J.C. Penney lost 40% within a day or two of announcing earnings disappointments.
     Waste Management continues to struggle through consolidation  problems, the
loss of its CEO,  who stepped  down due to  illness,  and  problems  with legacy
accounting systems. Management twice lowered earnings expectations, causing Wall
Street  to lose  confidence.  The  directors  have  stepped  in and are  selling
underperforming  assets, hiring consultants to solve the information  technology
problems, and bringing on a new CEO with an outstanding reputation.
     Raytheon  recently  acquired  E-Systems,  Hughes,  and a division  of Texas
Instruments,  and has been one of the fastest-growing and highest-margin defense
companies.  In September,  its new chairman  announced  that Raytheon would take
additional  restructuring  charges and that its revenue was slipping  because of
procurement  delays by the U.S.  Defense  Department  and  foreign  governments.
Raytheon's market-leading
- -------------------------------------------
INVESTMENT PHILOSOPHY
The fund reflects a belief that
superior  long-term  investment
results can be achieved  by  holding
a  diversified  portfolio  of  out-of-favor
stocks  with below-average  price/
earnings  ratios,  above-average
dividend yields,  and the prospect
of above-average total return.
- -------------------------------------------
                                       8
<PAGE>
products, combined with projected increases in defense spending, will drive this
stock going forward.
     Xerox  suffered from falling prices in the digital copier market and higher
expenses  associated  with  its new  "Solutions  Approach"  sales  program.  The
management had been unwilling or unable to inform the investment community about
problems,  and investors  dumped the stock.  We feel this  situation can improve
fairly soon.
     We purchased Allstate because of its industry-leading  position,  improving
business mix, low-cost operations, energized management, and powerful generation
of cash (which it is using to make  acquisitions and buy back stock).  The stock
was selling at a huge  discount to the market  based on its  price/earnings  and
price/book  ratios.  Still,  Allstate  operates in a competitive and challenging
industry.  In 1999, price  competition  remained high, claims costs rose (partly
due to Hurricane Floyd), and management decided to substantially boost marketing
expenditures to sell auto insurance on the Internet and via 800-type  offerings.
The net effect was that earnings estimates fell by about 15%--but the stock fell
twice as much!  Allstate now sells for less than 9 times current earnings,  at a
mere 12% premium to book value. It has a 2.5% dividend yield.
     Service Corporation International,  the world's largest funeral company, is
undergoing a transformation from an acquisition story to an operational one. Its
investments  in personnel,  training,  and  infrastructure  have raised  current
costs,  but will have  substantial  future  benefits.  Several other factors are
hurting revenue growth: Death rates have declined; price competition is tougher;
and there is a trend  toward  cremations.  However,  we  believe  the stock will
perform  much  better  as the  company's  transformation  is  completed  and the
environment improves.
     J.C. Penney stock fell due to  disappointing  sales growth and expectations
that higher interest rates will slow consumer spending.  The company is going to
spin off the Eckerd drug stores, and we expect results to improve.
     These six companies are industry leaders providing real services.  However,
they have lost  earnings  and price  momentum,  which  leads  believers  in Wall
Street's   "new   paradigm"   to  sell  them.  A  number  of  stocks  that  have
underperformed  are now  significantly  undervalued  and  have  become  takeover
targets for companies that will seek to turn them around and/or sell off pieces.
     The question arises: "What is the value in value investing?" We continue to
believe that price is a very important component of any buying decision, whether
a stock or a meal.  In relation to the broad  market,  our  holdings are cheaper
than  at  almost  any  time  in  the  past.  On  an  industry   basis,  we  have
concentrations in banks, energy, utilities, and insurance. Our underweighting in
technology   reflects   the  fact   that  few  of  those   issues   have   value
characteristics.  We have been through  periods  like this before,  though those
memories are not nearly so painful as 1999.  For the most part,  we are sticking
with our holdings. Indeed, we're adding to the cheaper ones.

Barrow, Hanley, Mewhinney & Strauss, Inc.

November 12, 1999

                                       9
<PAGE>
FUND PROFILE
WINDSOR II FUND

This Profile provides a snapshot of the fund's characteristics as of October 31,
1999,  compared where  appropriate to an unmanaged  index.  Key elements of this
Profile are defined on page 11.
- ---------------------------------------------
PORTFOLIO CHARACTERISTICS
- ---------------------------------------------
                      WINDSOR II      S&P 500
- ---------------------------------------------
Number of Stocks             282          500
Median Market Cap         $28.3B       $72.6B
Price/Earnings Ratio       18.0x        27.7x
Price/Book Ratio            2.7x         5.1x
Yield                       2.4%         1.2%
Return on Equity           18.8%        23.0%
Earnings Growth Rate        8.6%        15.0%
Foreign Holdings            1.4%         1.5%
Turnover Rate                26%          --
Expense Ratio              0.37%          --
Cash Reserves               3.2%          --

INVESTMENT FOCUS
- ---------------------------------------------
[GRID]
STYLE.........VALUE
MARKET CAP....LARGE

VOLATILITY MEASURES
- ---------------------------------------------
                      WINDSOR II      S&P 500
- ---------------------------------------------
R-Squared                   0.87         1.00
Beta                        0.90         1.00

TEN LARGEST HOLDINGS
(% OF TOTAL NET ASSETS)
- ---------------------------------------------
The Chase Manhattan Corp.                3.2%
Bank of America Corp.                    2.9
SBC Communications Inc.                  2.7
GTE Corp.                                2.7
Honeywell, Inc.                          2.5
Atlantic Richfield Co.                   2.4
Citigroup, Inc.                          2.1
Washington Mutual, Inc.                  2.1
Anheuser-Busch Cos., Inc.                2.1
Baker Hughes, Inc.                       2.0
Top Ten                                 24.7%

SECTOR DIVERSIFICATION (% OF COMMON STOCKS)
- --------------------------------------------------------------------------------
                                  OCTOBER 31, 1998          OCTOBER 31, 1999
- --------------------------------------------------------------------------------
                                      WINDSOR II        WINDSOR II       S&P 500
- --------------------------------------------------------------------------------
Auto & Transportation ............       4.8%              3.4%             2.2%
Consumer Discretionary ...........      11.0              10.7             12.5
Consumer Staples .................       8.4               6.9              7.2
Financial Services ...............      24.0              27.9             16.1
Health Care ......................       1.8               2.6             11.0
Integrated Oils ..................       3.6               7.4              5.2
Other Energy .....................       7.9               8.5              1.4
Materials & Processing ...........       3.7               4.2              3.2
Producer Durables ................       4.8               4.5              3.3
Technology .......................       3.6               4.4             20.5
Utilities ........................      18.5              15.1             11.2
Other ............................       7.9               4.4              6.2
- --------------------------------------------------------------------------------

                                       10
<PAGE>
BETA. A measure of the magnitude of a fund's past  share-price  fluctuations  in
relation  to the ups and downs of the  overall  market  (or  appropriate  market
index).  The market (or index) is assigned a beta of 1.00, so a fund with a beta
of 1.20  would have seen its share  price  rise or fall by 12% when the  overall
market rose or fell by 10%.

CASH  RESERVES.  The  percentage  of a  fund's  net  assets  invested  in  "cash
equivalents"--highly  liquid,  short-term,   interest-bearing  securities.  This
figure does not include cash  invested in futures  contracts  to simulate  stock
investment.

EARNINGS  GROWTH RATE.  The average  annual rate of growth in earnings  over the
past five years for the stocks now in a fund.

EXPENSE  RATIO.  The  percentage of a fund's  average net assets used to pay its
annual  administrative  and advisory  expenses.  These expenses  directly reduce
returns to investors.

FOREIGN HOLDINGS. The percentage of a fund's equity assets represented by stocks
or American Depositary Receipts of companies based outside the United States.

INVESTMENT  FOCUS.  This  grid  indicates  the  focus  of a fund in terms of two
attributes:  market  capitalization  (large,  medium,  or  small)  and  relative
valuation (growth, value, or a blend).

MEDIAN  MARKET  CAP.  An  indicator  of the  size of  companies  in which a fund
invests;  the  midpoint  of  market   capitalization   (market  price  x  shares
outstanding) of a fund's stocks, weighted by the proportion of the fund's assets
invested  in each  stock.  Stocks  representing  half of the fund's  assets have
market capitalizations above the median, and the rest are below it.

NUMBER OF STOCKS. An indicator of diversification. The more stocks a fund holds,
the more  diversified  it is and the more  likely  to  perform  in line with the
overall stock market.

PRICE/BOOK  RATIO.  The share price of a stock divided by its net worth, or book
value,  per share.  For a fund,  the weighted  average  price/book  ratio of the
stocks it holds.  Price/Earnings  Ratio. The ratio of a stock's current price to
its per-share  earnings over the past year. For a fund, the weighted average P/E
of the  stocks it  holds.  P/E is an  indicator  of  market  expectations  about
corporate  prospects;  the higher the P/E,  the greater the  expectations  for a
company's future growth.

R-SQUARED.  A measure of how much of a fund's past  returns can be  explained by
the returns from the overall market (or its benchmark  index). If a fund's total
return  were  precisely  synchronized  with the  overall  market's  return,  its
R-squared  would  be 1.00.  If a  fund's  returns  bore no  relationship  to the
market's returns, its R-squared would be 0.

RETURN ON  EQUITY.  The annual  average  rate of return  generated  by a company
during the past five years for each dollar of  shareholder's  equity (net income
divided by  shareholder's  equity).  For a fund, the weighted  average return on
equity for the companies whose stocks it holds.

SECTOR DIVERSIFICATION. The percentages of a fund's common stocks that come from
each of the major industry groups that compose the stock market.

TEN LARGEST  HOLDINGS.  The percentage of net assets that a fund has invested in
its ten largest holdings.  (The average for stock mutual funds is about 35%.) As
this percentage  rises, a fund's returns are likely to be more volatile  because
they are more dependent on the fortunes of a few companies.

TURNOVER  RATE. An indication of trading  activity  during the past year.  Funds
with high turnover rates incur higher  transaction  costs and are more likely to
distribute capital gains (which are taxable to investors).

YIELD.  A snapshot of a fund's  income from interest and  dividends.  The yield,
expressed  as a  percentage  of the fund's net asset  value,  is based on income
earned over the past 30 days and is  annualized,  or  projected  forward for the
coming  year.  The  index  yield  is  based on the  current  annualized  rate of
dividends paid on stocks in the index.

                                       11
<PAGE>
PERFORMANCE SUMMARY
WINDSOR II FUND

All of the data on this page represent past performance, which cannot be used to
predict  future returns that may be achieved by the fund.  Note,  too, that both
share  price and  return  can  fluctuate  widely.  An  investor's  shares,  when
redeemed, could be worth more or less than their original cost.

TOTAL INVESTMENT RETURNS: JUNE 24, 1985-OCTOBER 31, 1999
- ---------------------------------------|----------------------------------------
           WINDSOR II FUND     S&P 500 |             WINDSOR II FUND    S&P 500
FISCAL CAPITAL INCOME  TOTAL   TOTAL   |FISCAL CAPITAL INCOME  TOTAL    TOTAL
YEAR   RETURN  RETURN  RETURN  RETURN  |YEAR   RETURN  RETURN  RETURN   RETURN
- ---------------------------------------|----------------------------------------
1985   -0.9%   1.1%     0.2%    1.8%   |1993   15.8%    3.7%   19.5%    14.9%
1986   31.2    4.4     35.6    33.2    |1994   -0.8     3.0     2.2      3.9
1987   -0.6    1.5      0.9     6.4    |1995   19.2     3.9    23.1     26.4
1988   14.5    6.0     20.5    14.8    |1996   23.8     3.4    27.2     24.1
1989   19.5    5.2     24.7    26.4    |1997   28.1     3.2    31.3     32.1
1990   -21.5   4.0    -17.5    -7.5    |1998   14.1     2.4    16.5     22.0
1991   29.4    7.2     36.6    33.5    |1999    2.2     2.4     4.6     25.7
1992   7.9     4.6     12.5    10.0    |
- ---------------------------------------|----------------------------------------
See  FINANCIAL  HIGHLIGHTS  table  on page 19 for  dividend  and  capital  gains
information for the past five years.

CUMULATIVE PERFORMANCE: OCTOBER 31, 1989 -- OCTOBER 31, 1999
[MOUNTAIN CHART]
- --------------------------------------------------------------------------------
                  WINDSOR II    AVERAGE LARGE-CAP   S&P 500
                     FUND           VALUE FUND       INDEX
- --------------------------------------------------------------------------------
1989/10             10000             10000           10000
1990/01              9614              9681            9747
1990/04              9382              9770            9882
1990/07              9763             10463           10738
1990/10              8252              8965            9252
1991/01              9733             10401           10566
1991/04             10779             11322           11623
1991/07             11168             11729           12108
1991/10             11273             12106           12351
1992/01             11785             12704           12963
1992/04             12216             12931           13253
1992/07             12747             13142           13656
1992/10             12683             13128           13581
1993/01             13527             13964           14334
1993/04             13860             14238           14478
1993/07             14449             14578           14849
1993/10             15157             15483           15610
1994/01             15567             16037           16180
1994/04             14763             15189           15248
1994/07             15100             15404           15615
1994/10             15493             15917           16214
1995/01             15396             15812           16266
1995/04             16911             17275           17911
1995/07             18204             18724           19692
1995/10             19069             19423           20501
1996/01             21407             21230           22555
1996/04             22317             22008           23323
1996/07             21920             21448           22954
1996/10             24250             23741           25441
1997/01             26848             26244           28497
1997/04             27138             26559           29184
1997/07             31954             31345           34922
1997/10             31835             30500           33610
1998/01             33519             32162           36165
1998/04             38787             35948           41169
1998/07             37820             35210           41657
1998/10             37092             34883           41001
1999/01             39817             39029           47915
1999/04             43497             41258           50154
1999/07             41820             40773           50073
1999/10             38787             41026           51526
- --------------------------------------------------------------------------------
                               AVERAGE ANNUAL TOTAL RETURNS
                              PERIODS ENDED OCTOBER 31, 1999
                           ------------------------------------ FINAL VALUE OF A
                                1 YEAR    5 YEARS   10 YEARS  $10,000 INVESTMENT
- --------------------------------------------------------------------------------
Windsor II Fund                  4.57%     20.15%     14.52%             $38,787
Average Large-Cap Value Fund*   17.61      20.85      15.16               41,026
S&P 500 Index                   25.67      26.02      17.82               51,526
- --------------------------------------------------------------------------------
*Derived from data provided by Lipper Inc.

AVERAGE ANNUAL TOTAL RETURNS: PERIODS ENDED SEPTEMBER 30, 1999*
- --------------------------------------------------------------------------------
                                                              10 YEARS
                   INCEPTION                        ----------------------------
                     DATE      1 YEAR     5 YEARS   CAPITAL     INCOME    TOTAL
- --------------------------------------------------------------------------------
Windsor II Fund    6/24/1985    10.33%     20.10%    10.19%      3.75%    13.94%
- --------------------------------------------------------------------------------
*SEC rules require that we provide this average annual total return  information
through the last calendar quarter.

                                       12
<PAGE>
FINANCIAL STATEMENTS
OCTOBER 31, 1999

STATEMENT OF NET ASSETS
This Statement  provides a detailed list of the fund's holdings,  including each
security's market value on the last day of the reporting period.  Securities are
grouped  and  subtotaled  by asset  type  (common  stocks,  bonds,  etc.) and by
industry sector. Other assets are added to, and liabilities are subtracted from,
the value of TOTAL INVESTMENTS to calculate the fund's NET ASSETS.  Finally, NET
ASSETS are divided by the outstanding  shares of the fund to arrive at its share
price, or NET ASSET VALUE (NAV) PER SHARE.
     At the end of the Statement of Net Assets, you will find a table displaying
the  composition of the fund's net assets on both a dollar and per-share  basis.
Because all income and any realized gains must be  distributed  to  shareholders
each year, the bulk of net assets consists of PAID IN CAPITAL (money invested by
shareholders).  The amounts shown for  UNDISTRIBUTED  NET INVESTMENT  INCOME and
ACCUMULATED  NET  REALIZED  GAINS  usually  approximate  the  sums  the fund had
available to distribute to shareholders as income  dividends or capital gains as
of  the  statement  date,  but  may  differ  because   certain   investments  or
transactions  may  be  treated  differently  for  financial  statement  and  tax
purposes.  Any ACCUMULATED  NET REALIZED  LOSSES,  and any cumulative  excess of
distributions  over net income or net  realized  gains,  will appear as negative
balances.  UNREALIZED APPRECIATION  (DEPRECIATION) is the difference between the
market value of the fund's  investments  and their cost,  and reflects the gains
(losses) that would be realized if the fund were to sell all of its  investments
at their statement-date values.
- --------------------------------------------------------------------------------
                                                                          MARKET
                                                                          VALUE*
                                                    SHARES                 (000)
- --------------------------------------------------------------------------------
WINDSOR II FUND
- --------------------------------------------------------------------------------
COMMON STOCKS (92.9%)+
- --------------------------------------------------------------------------------
AUTO & TRANSPORTATION (3.1%)
         Ford Motor Co.                          8,675,800              476,085
         General Motors Corp.                    5,972,300              419,554
         Burlington Northern Santa Fe Corp.        333,300               10,624
         Delta Air Lines, Inc.                     151,600                8,253
         Tidewater Inc.                            224,600                6,738
o        UAL Corp.                                  88,900                6,051
         TRW, Inc.                                 141,100                6,050
         PACCAR, Inc.                              122,300                5,763
o        Continental Airlines, Inc. Class B        128,000                5,184
o        SPX Corp.                                  59,400                5,034
o        Navistar International Corp.              117,300                4,890
         Autoliv, Inc.                             146,470                4,678
         Cooper Tire & Rubber Co.                   98,600                1,658
                                                                     -----------
                                                                        960,562
                                                                     -----------
CONSUMER DISCRETIONARY (9.9%)
o(1)     Kmart Corp.                            41,622,500              418,826
         Waste Management, Inc.                 22,355,297              410,779
         Sears, Roebuck & Co.                   14,335,200              404,073
         Gannett Co., Inc.                       4,105,200              316,614
         Wal-Mart Stores, Inc.                   5,282,300              299,440
(1)      Service Corp. International            23,045,900              220,376
         Time Warner, Inc.                       2,491,000              173,592
o        The Walt Disney Co.                     6,074,932              160,226
         J.C. Penney Co., Inc.                   5,878,200              149,159
         Eastman Kodak Co.                       1,942,700              133,925
         Kimberly-Clark Corp.                    1,728,200              109,093
         Newell Rubbermaid, Inc.                 2,990,600              103,550
         Dayton Hudson Corp.                       680,300               43,964
o        Viacom Inc. Class B                       200,800                8,986
- --------------------------------------------------------------------------------
                                                                          MARKET
                                                                          VALUE*
                                                    SHARES                 (000)
- --------------------------------------------------------------------------------
         Hasbro, Inc.                              321,200                6,625
o        AT&T Corp.-Liberty Media Group Class A    152,000                6,033
         The Limited, Inc.                         141,200                5,807
o        Tricon Global Restaurants, Inc.           143,300                5,759
         Darden Restaurants Inc.                   295,100                5,625
o        Mandalay Resort Group                     274,500                5,113
         Galileo International, Inc.               166,400                5,002
         McDonald's Corp.                          120,600                4,975
         R.R. Donnelley & Sons Co.                 203,600                4,937
         Premark International, Inc.                85,700                4,692
o        Toys R Us, Inc.                           294,800                4,164
         Maytag Corp.                              100,300                4,018
o        Cendant Corp.                             213,600                3,524
         The Warnaco Group, Inc. Class A           226,600                3,229
         May Department Stores Co.                  74,037                2,568
         American Greetings Corp. Class A           98,600                2,551
o        Outback Steakhouse Inc.                    85,300                1,962
o        The Neiman Marcus Group, Inc. Class A      55,600                1,331
         Dillard's Inc.                             68,800                1,299
         VF Corp.                                   24,300                  731
o        ACNielson Corp.                            28,600                  629
         IKON Office Solutions, Inc.                58,500                  402
         Hertz Corp. Class A                         5,200                  226
                                                                     -----------
                                                                      3,033,805
                                                                     -----------
CONSUMER STAPLES (6.4%)
         Anheuser-Busch Cos., Inc.               8,956,000              643,153
         Philip Morris Cos., Inc.               22,592,000              569,036
         Imperial Tobacco Group ADR             12,448,100              259,854

                                       13
<PAGE>
- --------------------------------------------------------------------------------
                                                                          MARKET
                                                                          VALUE*
WINDSOR II FUND                                     SHARES                 (000)
- --------------------------------------------------------------------------------
         PepsiCo, Inc.                           6,186,600              214,598
         H.J. Heinz Co.                          2,802,200              133,805
         Sara Lee Corp.                          2,896,300               78,381
         Nabisco Group Holdings Corp.            3,220,600               41,264
         IBP, Inc.                                 249,700                5,977
         Tyson Foods, Inc.                         294,400                4,490
         SuperValu Inc.                            157,000                3,297
         ConAgra, Inc.                              50,000                1,303
         Brown-Forman Corp. Class B                 15,100                1,019
         Dean Foods Corp.                            9,900                  458
                                                                     -----------
                                                                      1,956,635
                                                                     -----------
FINANCIAL SERVICES (26.0%)
         BANKS--NEW YORK CITY (3.4%)
         The Chase Manhattan Corp.              11,352,956              991,965
         The Bank of New York Co., Inc.            366,400               15,343
         J.P. Morgan & Co., Inc.                   104,400               13,663
         Republic New York Corp.                    90,700                5,731
         BANKS--OUTSIDE NEW YORK CITY (10.1%)
         Bank of America Corp.                  13,714,212              882,852
         First Union Corp.                      13,769,602              587,790
         PNC Bank Corp.                          9,687,900              577,641
         Bank One Corp.                         11,199,283              420,673
         Wells Fargo Co.                         8,329,100              398,756
         SunTrust Banks, Inc.                    1,687,000              123,467
         Fleet Boston Corp.                        443,084               19,330
         Wachovia Corp.                            130,200               11,230
         KeyCorp                                   327,200                9,141
         AmSouth Bancorp                           278,100                7,161
         UnionBanCal Corp.                         146,678                6,371
         Old Kent Financial Corp.                  145,500                5,929
         Pacific Century Financial Corp.           203,000                4,631
         City National Corp.                       105,400                4,084
         Peoples Heritage Financial Group Inc.     170,300                3,236
         U.S. Bancorp                               86,300                3,198
         Huntington Bancshares Inc.                 99,400                2,945
         SouthTrust Corp.                           61,300                2,452
         Commerce Bancshares, Inc.                  34,860                1,351
         Provident Financial Group, Inc.            29,600                1,271
         National City Corp.                        27,900                  823

         DIVERSIFIED FINANCIAL SERVICES (3.4%)
         Citigroup, Inc.                        12,070,880              653,336
         Morgan Stanley Dean Witter & Co.        1,773,800              195,672
         American General Corp.                  1,965,400              145,808
         Merrill Lynch & Co., Inc.                 200,300               15,724
         PaineWebber Group, Inc.                   155,100                6,320
         The CIT Group, Inc.                       216,900                5,178
         American Express Co.                       23,700                3,650
         Marsh & McLennan Cos., Inc.                13,900                1,099
         Household International, Inc.              17,400                  776

         FINANCE COMPANIES
         Mellon Financial Corp.                    325,400               12,019
o        FIRSTPLUS Financial Group, Inc.           319,300                   42

         FINANCIAL DATA PROCESS SERVICES
         First Data Corp.                          126,900                5,798
         Deluxe Corp.                              176,000                4,972
o        DST Systems, Inc.                          53,000                3,375
- --------------------------------------------------------------------------------
                                                                          MARKET
                                                                          VALUE*
                                                    SHARES                 (000)
- --------------------------------------------------------------------------------
         FINANCIAL INFORMATION SERVICES
         Dow Jones & Co., Inc.                      98,000                6,027
         Dun & Bradstreet Corp.                    107,400                3,155
         FINANCIAL MISCELLANEOUS (1.7%)
         Fannie Mae                              7,173,500              507,525
         Nationwide Financial Services, Inc.       134,400                5,090
         AMBAC Financial Group Inc.                 73,900                4,416
         Associates First Capital Corp.             24,900                  909

         INSURANCE--LIFE
         Jefferson-Pilot Corp.                     118,300                8,880

         INSURANCE--MULTILINE (4.9%)
         Allstate Corp.                         19,282,044              554,359
(1)      Aon Corp.                              13,202,862              468,702
         American International Group, Inc.      4,186,361              430,934
         The Hartford Financial Services
           Group Inc.                              185,600                9,616
         CIGNA Corp.                               118,000                8,821
         Hartford Life, Inc.                       122,000                6,375
         Old Republic International Corp.          267,100                3,656
         American National Insurance Co.             4,700                  322

         INSURANCE--PROPERTY-CASUALTY (0.1%)
         Travelers Property Casualty Corp.         188,200                6,775
         The PMI Group Inc.                        109,350                5,673
         Everest Reinsurance Holdings, Inc.        152,900                3,937

         REAL ESTATE INVESTMENT TRUST (0.1%)
         Equity Office Properties Trust REIT       309,400                6,845
         Equity Residential Properties Trust REIT  158,100                6,611
         Simon Property Group, Inc. REIT           197,000                4,543
         Host Marriott Corp. REIT                  434,300                3,909
         Spieker Properties, Inc. REIT              43,500                1,520

         RENT & LEASE SERVICES--COMMERCIAL
         Ryder System, Inc.                        227,200                4,856

         SAVINGS & LOAN (2.2%)
         Washington Mutual, Inc.                17,993,194              646,630
         Golden West Financial Corp.                65,600                7,331
o        Golden State Bancorp Inc.                 298,400                6,229
         Dime Bancorp, Inc.                        309,000                5,523
         Sovereign Bancorp, Inc.                   506,600                4,464
         Charter One Financial, Inc.                59,745                1,467
         Peoples Bank Bridgeport                    47,000                1,190

         SECURITIES BROKERS & SERVICES (0.1%)
         Bear Stearns Co., Inc.                    171,000                7,289
         A.G. Edwards & Sons, Inc.                 229,850                6,910
         Legg Mason Inc.                           145,600                5,296
         Countrywide Credit Industries, Inc.       148,800                5,050
                                                                     -----------
                                                                      7,915,638
                                                                     -----------

                                       14
<PAGE>
- --------------------------------------------------------------------------------
                                                                          MARKET
                                                                          VALUE*
                                                    SHARES                 (000)
- --------------------------------------------------------------------------------
HEALTH CARE (2.4%)
         American Home Products Corp.            4,861,900              254,034
         Bristol-Myers Squibb Co.                2,254,000              173,135
         Columbia/HCA Healthcare Corp.           6,676,500              161,071
         Aetna Inc.                              1,831,500               92,033
         Abbott Laboratories                       296,000               11,951
         United Healthcare Corp.                   119,300                6,166
         Johnson & Johnson                          54,600                5,719
o        Chiron Corp.                              188,900                5,395
o        IVAX Corp.                                298,600                5,244
         C.R. Bard, Inc.                            96,100                5,183
o        Tenet Healthcare Corp.                    251,900                4,896
         Mylan Laboratories, Inc.                  241,600                4,334
         Pharmacia & Upjohn, Inc.                   69,700                3,759
o        Genzyme Corp.                              13,200                  505
                                                                     -----------
                                                                        733,425
                                                                     -----------
INTEGRATED OILS (6.9%)
         Atlantic Richfield Co.                  8,029,000              748,202
(1)      Occidental Petroleum Corp.             20,894,900              476,665
         Phillips Petroleum Co.                  9,517,500              442,564
         Mobil Corp.                             1,980,100              191,080
         Exxon Corp.                             2,466,100              182,646
         Conoco Inc. Class B                     1,341,500               36,388
         Chevron Corp.                             177,200               16,181
         Texaco Inc.                               111,200                6,825
         Amerada Hess Corp.                        109,100                6,260
                                                                     -----------
                                                                      2,106,811
                                                                     -----------
OTHER ENERGY (7.9%)
(1)      Baker Hughes, Inc.                     21,645,400              604,718
         Schlumberger Ltd.                       8,854,500              536,251
         Halliburton Co.                        14,083,900              530,787
         Williams Cos., Inc.                    13,044,046              489,152
         Enron Corp.                             5,502,600              219,760
         Tosco Corp.                               261,100                6,609
         Apache Corp.                              117,200                4,571
         Ashland, Inc.                             122,700                4,049
         Sunoco, Inc.                              159,000                3,836
         Ultramar Diamond Shamrock Corp.           145,700                3,570
         Union Pacific Resources Group, Inc.       198,900                2,884
         EOG Resources, Inc.                        81,700                1,700
         Dynegy, Inc.                               30,500                  698
                                                                     -----------
                                                                      2,408,585
                                                                     -----------
MATERIALS & PROCESSING (3.9%)
(1)      Fort James Corp.                       18,728,600              492,796
(1)      Millennium Chemicals, Inc.              7,719,942              142,819
         Phelps Dodge Corp.                      2,523,400              142,257
         Dow Chemical Co.                        1,187,100              140,375
         Hanson PLC ADR                          3,426,750              132,572
         CK Witco Corp.                          5,020,069               47,063
         E.I. du Pont de Nemours & Co.             212,787               13,711
         The Mead Corp.                            179,500                6,462
         The Timber Co.                            258,000                6,160
         Praxair, Inc.                             130,800                6,115
         USG Corp.                                 119,000                5,898
         USX-U.S. Steel Group                      228,800                5,849
         Lafarge Corp.                             171,000                5,077
- --------------------------------------------------------------------------------
                                                                          MARKET
                                                                          VALUE*
                                                    SHARES                 (000)
- --------------------------------------------------------------------------------
         Solutia, Inc.                             286,600                4,926
         Avery Dennison Corp.                       63,500                3,969
         Louisiana-Pacific Corp.                   284,300                3,607
         Armstrong World Industries Inc.            96,500                3,607
         Engelhard Corp.                           190,100                3,351
         Boise Cascade Corp.                        92,400                3,292
         IMC Global Inc.                           224,000                2,856
         Alcoa Inc.                                 41,800                2,539
         Johns Manville Corp.                      220,000                2,406
         International Paper Co.                    29,200                1,537
         Owens Corning                              30,800                  631
         Westvaco Corp.                             18,500                  549
                                                                     -----------
                                                                      1,180,424
                                                                     -----------
PRODUCER DURABLES (4.1%)
(1)      Honeywell, Inc.                         7,242,700              763,652
         Xerox Corp.                            13,739,742              384,713
         Lockheed Martin Corp.                   3,502,800               70,056
         Emerson Electric Co.                      135,900                8,162
         The Boeing Co.                            170,300                7,844
         United Technologies Corp.                 123,696                7,484
o        Teradyne, Inc.                            143,100                5,509
         Northrop Grumman Corp.                     73,300                4,022
         Pitney Bowes, Inc.                         86,600                3,946
         Molex, Inc.                                67,500                2,464
         Pentair, Inc.                              58,000                2,182
         Caterpillar, Inc.                          23,600                1,304
o        Howmet International Inc.                  77,100                1,137
         Centex Corp.                               40,800                1,094
         Diebold, Inc.                              32,300                  848
         Tecumseh Products Co. Class A               9,160                  439
         The BFGoodrich Co.                         15,100                  358
                                                                     -----------
                                                                      1,265,214
                                                                     -----------
TECHNOLOGY (4.1%)
         Electronic Data Systems Corp.           7,873,500              460,600
         Raytheon Co. Class B                   10,916,600              317,946
         Intel Corp.                             2,730,000              211,404
         International Business Machines Corp.   2,053,500              202,013
o        Apple Computer, Inc.                      129,100               10,344
         Motorola, Inc.                             86,800                8,458
o        Safeguard Scientifics, Inc.                85,300                7,176
o        National Semiconductor Corp.              217,100                6,499
o        General Instrument Corp.                  106,600                5,736
o        NCR Corp.                                 143,500                4,753
         Hewlett-Packard Co.                        55,000                4,073
o        SCI Systems, Inc.                          78,300                3,866
o        Seagate Technology Inc.                   109,200                3,215
o        SDL, Inc.                                  15,900                1,961
         Compaq Computer Corp.                      20,300                  386
                                                                     -----------
                                                                      1,248,430
                                                                     -----------
UTILITIES (14.0%)
         SBC Communications Inc.                16,023,947              816,220
         GTE Corp.                              10,872,600              815,445
(1)      Entergy Corp.                          19,851,400              594,301
(1)      American Electric Power Co., Inc.      10,090,300              348,115
         Reliant Energy, Inc.                   10,869,900              296,205
         FirstEnergy Corp.                      10,629,177              277,023
(1)      Central & South West Corp.             12,443,000              276,079
         AT&T Corp.                              4,613,317              215,673

                                       15
<PAGE>
- --------------------------------------------------------------------------------
                                                                          MARKET
                                                                          VALUE*
WINDSOR II FUND                                     SHARES                 (000)
- --------------------------------------------------------------------------------
o        MCI WorldCom, Inc.                      2,435,648              209,009
         Public Service Enterprise Group, Inc.   5,263,300              208,229
         BellSouth Corp.                           764,800               34,416
         Bell Atlantic Corp.                       467,136               30,335
         Sprint Corp.                              315,880               23,474
         Southern Co.                              415,600               11,039
         Telephone & Data Systems, Inc.             72,900                8,402
         Edison International                      283,200                8,390
o        MediaOne Group, Inc.                      110,200                7,831
         PG&E Corp.                                327,600                7,514
         CenturyTel, Inc.                          171,650                6,941
o        U.S. Cellular Corp.                        73,500                6,505
         GPU, Inc.                                 188,300                6,390
         Ameren Corp.                              168,200                6,360
o        Cox Communications, Inc. Class A          138,800                6,307
         Energy East Corp.                         248,000                6,231
         MidAmerican Energy Holdings Co.           184,900                6,217
         DTE Energy Co.                            187,100                6,209
         PP&L Resources Inc.                       222,288                6,016
         Constellation Energy Group                195,600                6,002
         Unicom Corp.                              140,700                5,391
         ALLTEL Corp.                               64,600                5,378
         Pinnacle West Capital Corp.               109,000                4,019
         Consolidated Edison Inc.                   99,200                3,788
         FPL Group, Inc.                            59,500                2,994
         Duke Energy Corp.                          46,700                2,639
o        Citizens Utilities Co. Class B            185,000                2,139
         Allegheny Energy, Inc.                     52,600                1,673
         Cinergy Corp.                              50,000                1,413
         U S WEST, Inc.                             10,300                  629
         PECO Energy Corp.                          15,000                  573
                                                                     -----------
                                                                      4,281,514
                                                                     -----------
OTHER (4.2%)
         General Electric Co.                    2,784,200              377,433
         AlliedSignal Inc.                       5,603,200              319,032
(1)      ITT Industries, Inc.                    9,282,100              317,332
(1)      Tenneco, Inc.                          13,588,800              217,421
         Minnesota Mining & Manufacturing Co.      230,500               21,912
         Textron, Inc.                              97,300                7,510
         Loews Corp.                                63,000                4,465
         Johnson Controls, Inc.                     57,500                3,493
         Fortune Brands, Inc.                       70,800                2,509
         Brunswick Corp.                            98,600                2,231
         Crane Co.                                  91,950                1,879
o        FMC Corp.                                  38,800                1,579
         Lancaster Colony Corp.                     39,500                1,380
                                                                     -----------
                                                                      1,278,176
                                                                     -----------
- --------------------------------------------------------------------------------
TOTAL COMMON STOCKS
  (COST $22,960,628)                                                 28,369,219
- --------------------------------------------------------------------------------
- --------------------------------------------------------------------------------
                                                      FACE                MARKET
                                                    AMOUNT                VALUE*
                                                     (000)                 (000)
- --------------------------------------------------------------------------------
TEMPORARY CASH INVESTMENTS (7.4%)+
- --------------------------------------------------------------------------------
FEDERAL HOME LOAN MORTGAGE CORP.
(2)      5.57%, 2/3/2000                            10,000                9,843
FEDERAL NATIONAL MORTGAGE ASSN.
(2)      5.53%, 1/28/2000                           17,200               16,944
(2)      5.64%, 1/21/2000                           55,000               54,246
REPURCHASE AGREEMENTS
Collateralized by U.S. Government
         Obligations in a Pooled
         Cash Account
         5.24%, 11/1/1999                        2,170,817            2,170,817
         5.26%, 11/1/1999--Note G                    2,215                2,215
- --------------------------------------------------------------------------------
TOTAL TEMPORARY CASH INVESTMENTS
  (COST $2,254,166)                                                   2,254,065
- --------------------------------------------------------------------------------
TOTAL INVESTMENTS (100.3%)
  (COST $25,214,794)                                                 30,623,284
- --------------------------------------------------------------------------------
OTHER ASSETS AND LIABILITIES (-0.3%)
- --------------------------------------------------------------------------------
Other Assets--Note C                                                    125,688
Liabilities--Note G                                                    (208,143)
                                                                     -----------
                                                                        (82,455)
- --------------------------------------------------------------------------------
NET ASSETS (100%)
- --------------------------------------------------------------------------------
Applicable to 1,051,864,256 outstanding $.001
         par value shares of beneficial interest
         (unlimited authorization)                                  $30,540,829
================================================================================
NET ASSET VALUE PER SHARE                                                $29.03
================================================================================
*    See Note A in Notes to Financial Statements.
o    Non-Income-Producing Security.
+    The fund invests a portion of its cash reserves in equity  markets  through
     the  use of  index  futures  contracts.  After  giving  effect  to  futures
     investments,   the  fund's   effective  common  stock  and  temporary  cash
     investment positions represent 96.8% and 3.5%, respectively, of net assets.
     See Note F in Notes to Financial Statements.
(1)  Considered  an  affiliated  company  as the fund  owns  more than 5% of the
     outstanding  voting  securities of such company.  The total market value of
     investments in affiliated companies was $5,341,802,000.
(2)  Security segregated as initial margin for open futures contracts.
ADR--American Depositary Receipt.
REIT--Real Estate Investment Trust.
- --------------------------------------------------------------------------------
AT OCTOBER 31, 1999, NET ASSETS CONSISTED OF:
- --------------------------------------------------------------------------------
                                                    AMOUNT                   PER
                                                     (000)                 SHARE
- --------------------------------------------------------------------------------
Paid in Capital                                $22,391,512                $21.28
Undistributed Net
     Investment Income                             223,131                   .21
Accumulated Net
     Realized Gains                              2,498,602                  2.38
Unrealized Appreciation--
     Note F
     Investment Securities                       5,408,490                  5.14
     Futures Contracts                              19,094                   .02
- --------------------------------------------------------------------------------
NET ASSETS                                     $30,540,829                $29.03
================================================================================

                                       16
<PAGE>
STATEMENT OF OPERATIONS
This Statement  shows dividend and interest income earned by the fund during the
reporting period,  and details the operating expenses charged to the fund. These
expenses  directly  reduce the amount of investment  income  available to pay to
shareholders  as  dividends.  This  Statement  also  shows  any Net Gain  (Loss)
realized  on the  sale of  investments,  and the  increase  or  decrease  in the
Unrealized Appreciation  (Depreciation) on investments during the period. If the
fund  invested  in futures  contracts  during the  period,  the results of these
investments are shown separately.
- --------------------------------------------------------------------------------
                                                                 WINDSOR II FUND
                                                     YEAR ENDED OCTOBER 31, 1999
                                                                           (000)
- --------------------------------------------------------------------------------
INVESTMENT INCOME
INCOME
         Dividends*                                                     676,050
         Interest                                                       111,896
         Security Lending                                                   161
                                                                     -----------
                  Total Income                                          788,107
                                                                     -----------
EXPENSES
         Investment Advisory Fees--Note B
                  Basic Fee                                              39,214
                  Performance Adjustment                                 (1,642)
         The Vanguard Group--Note C
                  Management and Administrative                          76,419
                  Marketing and Distribution                              5,283
         Custodian Fees                                                      74
         Auditing Fees                                                       27
         Shareholders' Reports                                              732
         Trustees' Fees and Expenses                                         49
                                                                     -----------
                  Total Expenses                                        120,156
                  Expenses Paid Indirectly--Note D                       (2,051)
                                                                     -----------
                  Net Expenses                                          118,105
- --------------------------------------------------------------------------------
NET INVESTMENT INCOME                                                   670,002
- --------------------------------------------------------------------------------
REALIZED NET GAIN
         Investment Securities Sold*                                  2,259,982
         Futures Contracts                                              340,033
- --------------------------------------------------------------------------------
REALIZED NET GAIN                                                     2,600,015
- --------------------------------------------------------------------------------
CHANGE IN UNREALIZED APPRECIATION (DEPRECIATION)
         Investment Securities                                       (1,852,721)
         Futures Contracts                                              (78,391)
- --------------------------------------------------------------------------------
CHANGE IN UNREALIZED APPRECIATION (DEPRECIATION)                     (1,931,112)
- --------------------------------------------------------------------------------
NET INCREASE IN NET ASSETS RESULTING FROM OPERATIONS                 $1,338,905
================================================================================
*Dividend   income  and  realized  net  gain  from  affiliated   companies  were
$165,984,000 and $34,822,000, respectively.

                                       17
<PAGE>
STATEMENT OF CHANGES IN NET ASSETS
This Statement shows how the fund's total net assets changed during the two most
recent reporting periods. The Operations section summarizes information detailed
in  the  Statement  of  Operations.   The  amounts  shown  as  Distributions  to
shareholders  from the fund's net  income  and  capital  gains may not match the
amounts shown in the Operations section, because distributions are determined on
a tax  basis  and may be made in a period  different  from the one in which  the
income was earned or the gains were  realized on the financial  statements.  The
Capital Share Transactions section shows the amount shareholders invested in the
fund,  either by purchasing shares or by reinvesting  distributions,  as well as
the amounts redeemed.  The  corresponding  numbers of Shares Issued and Redeemed
are shown at the end of the Statement.
- --------------------------------------------------------------------------------
                                                             WINDSOR II FUND
                                                          YEAR ENDED OCTOBER 31,
                                                          ----------------------
                                                                1999        1998
                                                               (000)       (000)
- --------------------------------------------------------------------------------
INCREASE (DECREASE) IN NET ASSETS
OPERATIONS
  Net Investment Income                                      670,002     589,221
  Realized Net Gain                                        2,600,015   2,457,628
  Change in Unrealized Appreciation (Depreciation)       (1,931,112)     694,834
                                                          ----------------------
     Net Increase in Net Assets Resulting from Operations  1,338,905   3,741,683
                                                          ----------------------
DISTRIBUTIONS
  Net Investment Income                                    (741,695)   (541,835)
  Realized Capital Gain                                  (2,559,664) (1,694,611)
                                                          ----------------------
     Total Distributions                                 (3,301,359) (2,236,446)
                                                          ----------------------
CAPITAL SHARE TRANSACTIONS1
  Issued                                                   6,123,676   7,469,255
  Issued in Lieu of Cash Distributions                     3,148,067   2,144,820
  Redeemed                                               (6,407,121) (4,048,511)
                                                          ----------------------
     Net Increase from Capital Share Transactions          2,864,622   5,565,564
  Total Increase                                             902,168   7,070,801
- --------------------------------------------------------------------------------
NET ASSETS
  Beginning of Year                                       29,638,661  22,567,860
                                                          ----------------------
  End of Year                                            $30,540,829 $29,638,661
================================================================================
1Shares Issued (Redeemed)
  Issued                                                     198,010     243,421
  Issued in Lieu of Cash Distributions                       109,009      75,460
  Redeemed                                                 (209,049)   (133,672)
     Net Increase in Shares Outstanding                       97,970     185,209
================================================================================

                                       18
<PAGE>

FINANCIAL HIGHLIGHTS

This table  summarizes  the  fund's  investment  results  and  distributions  to
shareholders on a per-share  basis. It also presents the fund's Total Return and
shows net  investment  income and expenses as percentages of average net assets.
These data will help you assess:  the  variability  of the fund's net income and
total returns from year to year;  the relative  contributions  of net income and
capital gains to the fund's total return; how much it costs to operate the fund;
and the extent to which the fund tends to distribute  capital  gains.  The table
also  shows the  Portfolio  Turnover  Rate,  a measure of  trading  activity.  A
turnover  rate of 100% means that the  average  security is held in the fund for
one year.
<TABLE>
<CAPTION>
- -----------------------------------------------------------------------------------------------------------
                                                                             WINDSOR II FUND
                                                                          YEAR ENDED OCTOBER 31,
                                                             ----------------------------------------------
<S>                                                             <C>        <C>       <C>      <C>      <C>
FOR A SHARE OUTSTANDING THROUGHOUT EACH YEAR                    1999       1998      1997     1996     1995
- -----------------------------------------------------------------------------------------------------------
NET ASSET VALUE, BEGINNING OF YEAR                            $31.07     $29.36    $24.04   $20.06   $17.33
- -----------------------------------------------------------------------------------------------------------
INVESTMENT OPERATIONS
         Net Investment Income                                   .64        .65       .64      .62      .58
         Net Realized and Unrealized Gain (Loss) on Investments  .73       3.91      6.47     4.63     3.17
                                                             ----------------------------------------------
                  Total from Investment Operations              1.37       4.56      7.11     5.25     3.75
                                                             ----------------------------------------------
DISTRIBUTIONS

         Dividends from Net Investment Income                   (.74)      (.66)     (.63)    (.58)    (.55)
         Distributions from Realized Capital Gains             (2.67)     (2.19)    (1.16)    (.69)    (.47)
                  Total Distributions                          (3.41)     (2.85)    (1.79)   (1.27)   (1.02)
- -----------------------------------------------------------------------------------------------------------
NET ASSET VALUE, END OF YEAR                                  $29.03     $31.07    $29.36   $24.04   $20.06
===========================================================================================================
TOTAL RETURN                                                    4.57%     16.51%    31.27%   27.17%   23.08%
===========================================================================================================

RATIOS/SUPPLEMENTAL DATA
         Net Assets, End of Year (Millions)                  $30,541    $29,639   $22,568  $14,758  $10,272
         Ratio of Total Expenses to Average Net Assets          0.37%      0.41%     0.37%    0.39%    0.40%
         Ratio of Net Investment Income to Average Net Assets   2.08%      2.16%     2.49%    2.92%    3.27%
         Portfolio Turnover Rate                                  26%        31%       30%      32%      30%
===========================================================================================================
</TABLE>

                                       19
<PAGE>
NOTES TO FINANCIAL STATEMENTS
Vanguard Windsor II Fund is registered under the Investment  Company Act of 1940
as a diversified open-end investment company, or mutual fund.

A. The following  significant  accounting policies conform to generally accepted
accounting  principles  for mutual  funds.  The fund  consistently  follows such
policies in preparing its financial statements.
     1. SECURITY  VALUATION:  Equity  securities are valued at the latest quoted
sales  prices  as of the  close  of  trading  on the  New  York  Stock  Exchange
(generally  4:00 p.m.  Eastern time) on the valuation  date; such securities not
traded on the valuation date are valued at the mean of the latest quoted bid and
asked  prices.  Prices are taken from the primary  market in which each security
trades.  Temporary cash investments acquired over 60 days to maturity are valued
using the latest bid prices or using  valuations based on a matrix system (which
considers such factors as security  prices,  yields,  maturities,  and ratings),
both  as  furnished  by  independent  pricing  services.  Other  temporary  cash
investments  are valued at amortized  cost,  which  approximates  market  value.
Securities for which market  quotations are not readily  available are valued by
methods deemed by the Board of Trustees to represent fair value.
     2.  FEDERAL  INCOME  TAXES:  The fund  intends to  continue to qualify as a
regulated   investment  company  and  distribute  all  of  its  taxable  income.
Accordingly,  no provision for federal income taxes is required in the financial
statements.
     3.  REPURCHASE  AGREEMENTS:  The fund,  along  with  other  members  of The
Vanguard  Group,  transfers  uninvested  cash balances to a Pooled Cash Account,
which  is  invested  in  repurchase   agreements  secured  by  U.S.   government
securities.  Securities pledged as collateral for repurchase agreements are held
by a custodian bank until the agreements  mature.  Each agreement  requires that
the market value of the  collateral be sufficient to cover  payments of interest
and principal; however, in the event of default or bankruptcy by the other party
to  the  agreement,  retention  of  the  collateral  may  be  subject  to  legal
proceedings.
     4. FUTURES CONTRACTS:  The fund uses S&P 500 Index and S&P MidCap 400 Index
futures  contracts to a limited extent,  with the objective of maintaining  full
exposure to the stock market while maintaining liquidity.  The fund may purchase
or sell futures  contracts to achieve a desired level of investment,  whether to
accommodate  portfolio  turnover or cash flows from capital share  transactions.
The primary  risks  associated  with the use of futures  contracts are imperfect
correlation  between changes in market values of stocks held by the fund and the
prices of futures contracts, and the possibility of an illiquid market.
     Futures contracts are valued at their quoted daily settlement  prices.  The
aggregate  principal  amounts of the contracts are not recorded in the financial
statements.  Fluctuations  in the value of the  contracts  are  recorded  in the
Statement  of Net  Assets  as an  asset  (liability)  and in  the  Statement  of
Operations as  unrealized  appreciation  (depreciation)  until the contracts are
closed, when they are recorded as realized futures gains (losses).
     5.  DISTRIBUTIONS:  Distributions  to  shareholders  are  recorded  on  the
ex-dividend  date.  Distributions  are  determined on a tax basis and may differ
from net investment  income and realized  capital gains for financial  reporting
purposes.
     6. OTHER:  Dividend  income is recorded on the ex-dividend  date.  Security
transactions  are accounted for on the date securities are bought or sold. Costs
used to determine  realized gains (losses) on the sale of investment  securities
are those of the specific securities sold.

B. Barrow, Hanley, Mewhinney & Strauss, Inc.; Equinox Capital Management,  Inc.;
and Tukman Capital Management, Inc., provide investment advisory services to the
fund for fees calculated at an annual percentage rate of average net assets. The
basic fees thus  computed for Barrow,  Hanley,  Mewhinney & Strauss,  Inc.,  are
subject to quarterly  adjustments based on performance relative to the S&P/BARRA
Value Index;  such fees for Equinox  Capital  Management,  Inc.,  are subject to
quarterly  adjustments  based on performance  relative to the Russell 1000 Value
Index; such fees for Tukman Capital  Management,  Inc., are subject to quarterly
adjustments based on performance relative to the S&P 500 Index.

                                       20
<PAGE>
     The Vanguard Group provides  investment  advisory  services to a portion of
the fund on an at-cost basis;  the fund paid Vanguard  advisory fees of $511,000
for the year ended October 31, 1999.
     For the year ended October 31, 1999, the aggregate  investment advisory fee
represented an effective annual basic rate of 0.12% of average net assets before
a decrease of $1,642,000 (0.01%) based on performance.

C. The Vanguard Group  furnishes at cost corporate  management,  administrative,
marketing,  and distribution  services. The costs of such services are allocated
to the fund  under  methods  approved  by the  Board of  Trustees.  The fund has
committed to provide up to 0.40% of its net assets in capital  contributions  to
Vanguard. At October 31, 1999, the fund had contributed capital of $6,582,000 to
Vanguard (included in Other Assets), representing 0.02% of the fund's net assets
and 6.6% of Vanguard's capitalization. The fund's Trustees and officers are also
Directors and officers of Vanguard.

D. Vanguard has asked the fund's investment advisers to direct certain portfolio
trades,  subject to obtaining the best price and execution,  to brokers who have
agreed to rebate to the fund part of the commissions generated. Such rebates are
used solely to reduce the fund's  management and  administrative  expenses.  The
fund's custodian has also agreed to reduce its fees when the fund maintains cash
on  deposit  in the  non-interest-bearing  custody  account.  For the year ended
October 31, 1999, these  arrangements  reduced expenses by $2,045,000 and $6,000
respectively.  The total expense reduction  represented an effective annual rate
of 0.01% of the fund's average net assets.

E. During the year ended October 31, 1999, the fund purchased  $8,073,231,000 of
investment  securities and sold $7,658,527,000 of investment  securities,  other
than temporary cash investments.

F. At October 31, 1999, net unrealized appreciation of investment securities for
financial   reporting  and  federal  income  tax  purposes  was  $5,408,490,000,
consisting of unrealized gains of $8,450,647,000 on securities that had risen in
value since their purchase and $3,042,157,000 in unrealized losses on securities
that had fallen in value since their purchase.
     At  October  31,  1999,  the  aggregate  settlement  value of open  futures
contracts  expiring in December  1999 and the  related  unrealized  appreciation
(depreciation) were:
- --------------------------------------------------------------------------------
                                                           (000)
                                             -----------------------------------
                                               AGGREGATE           UNREALIZED
                            NUMBER OF         SETTLEMENT          APPRECIATION
FUTURES CONTRACTS        LONG CONTRACTS         VALUE            (DEPRECIATION)
- --------------------------------------------------------------------------------
S&P 500 Index                3,028            $1,041,783             $22,378
S&P MidCap 400 Index           710               142,444              (3,284)
- --------------------------------------------------------------------------------
Net unrealized  appreciation on open futures contracts is required to be treated
as realized gain for tax purposes.

G. The market value of securities on loan to broker/dealers at October 31, 1999,
was  $40,000,  for  which  the fund held cash  collateral  of  $2,215,000.  Cash
collateral received is invested in repurchase agreements.

                                       21
<PAGE>
REPORT OF INDEPENDENT ACCOUNTANTS

To the Shareholders and Trustees of
Vanguard Windsor II Fund

In our  opinion,  the  accompanying  statement  of net  assets  and the  related
statements  of  operations  and of  changes  in net  assets  and  the  financial
highlights present fairly, in all material  respects,  the financial position of
Vanguard  Windsor II Fund (the "Fund") at October 31,  1999,  the results of its
operations  for the year then  ended,  the changes in its net assets for each of
the two years in the period then ended and the financial  highlights for each of
the five years in the period then ended, in conformity  with generally  accepted
accounting  principles.  These  financial  statements  and financial  highlights
(hereafter referred to as "financial  statements") are the responsibility of the
Fund's  management;  our  responsibility  is to  express  an  opinion  on  these
financial  statements  based on our  audits.  We  conducted  our audits of these
financial  statements in accordance with generally  accepted auditing  standards
which require that we plan and perform the audit to obtain reasonable  assurance
about whether the financial  statements  are free of material  misstatement.  An
audit includes examining,  on a test basis,  evidence supporting the amounts and
disclosures in the financial  statements,  assessing the  accounting  principles
used and  significant  estimates made by management,  and evaluating the overall
financial  statement  presentation.  We believe that our audits,  which included
confirmation  of  securities  at October  31,  1999 by  correspondence  with the
custodian  and  brokers,  provide a reasonable  basis for the opinion  expressed
above.

PricewaterhouseCoopers LLP

Thirty South Seventeenth Street
Philadelphia, Pennsylvania 19103

November 30, 1999

                                       22
<PAGE>
- --------------------------------------------------------------------------------
SPECIAL 1999 TAX INFORMATION (UNAUDITED) FOR
VANGUARD WINDSOR II FUND

This  information  for the fiscal  year ended  October  31,  1999,  is  included
pursuant to provisions of the Internal Revenue Code.
     The fund  distributed  $2,166,607,000  as capital gain dividends  (from net
long-term  capital  gains) to  shareholders  in December  1998,  all of which is
designated as a 20% rate gain distribution.
     For corporate  shareholders,  61.2% of investment  income  (dividend income
plus short-term gains, if any) qualifies for the dividends-received deduction.
- --------------------------------------------------------------------------------

                                       23
<PAGE>

THE VANGUARD FAMILY OF FUNDS

STOCK FUNDS
- --------------------------------------------------------------------------------
500 Index Fund
Aggressive Growth Fund
Capital Opportunity Fund
Convertible Securities Fund
Emerging Markets Stock Index Fund
Energy Fund
Equity Income Fund
European Stock Index Fund
Explorer Fund
Extended Market Index Fund*
Global Equity Fund
Gold and Precious Metals Fund
Growth and Income Fund
Growth Index Fund*
Health Care Fund
Institutional Index Fund*
International Growth Fund
International Value Fund
Mid-Cap Index Fund*
Morgan Growth Fund
Pacific Stock Index Fund
PRIMECAP Fund
REIT Index Fund
Selected Value Fund
Small-Cap Growth Index Fund*
Small-Cap Index Fund*
Small-Cap Value Index Fund*
Tax-Managed Capital Appreciation Fund*
Tax-Managed Growth and Income Fund*
Tax-Managed International Fund
Tax-Managed Small-Cap Fund*
Total International Stock Index Fund
Total Stock Market Index Fund*
U.S. Growth Fund
Utilities Income Fund
Value Index Fund*
Windsor Fund
Windsor II Fund

BALANCED FUNDS
- --------------------------------------------------------------------------------
Asset Allocation Fund
Balanced Index Fund
Global Asset Allocation Fund
LifeStrategy Conservative Growth Fund
LifeStrategy Growth Fund
LifeStrategy Income Fund
LifeStrategy Moderate Growth Fund
STAR Fund
Tax-Managed Balanced Fund
Wellesley Income Fund
Wellington Fund

BOND FUNDS
- --------------------------------------------------------------------------------
Admiral Intermediate-Term Treasury Fund
Admiral Long-Term Treasury Fund
Admiral Short-Term Treasury Fund
GNMA Fund
High-Yield Corporate Fund
High-Yield Tax-Exempt Fund
Insured Long-Term Tax-Exempt Fund
Intermediate-Term Bond Index Fund
Intermediate-Term Corporate Fund
Intermediate-Term Tax-Exempt Fund
Intermediate-Term Treasury Fund
Limited-Term Tax-Exempt Fund
Long-Term Bond Index Fund
Long-Term Corporate Fund
Long-Term Tax-Exempt Fund
Long-Term Treasury Fund
Preferred Stock Fund
Short-Term Bond Index Fund
Short-Term Corporate Fund*
Short-Term Federal Fund
Short-Term Tax-Exempt Fund
Short-Term Treasury Fund
State Tax-Exempt Bond Funds
  (California, Florida, Massachusetts, New Jersey,
   New York, Ohio, Pennsylvania)
Total Bond Market Index Fund*

MONEY MARKET FUNDS
- --------------------------------------------------------------------------------
Admiral Treasury Money Market Fund
Federal Money Market Fund
Prime Money Market Fund*
State Tax-Exempt Money Market Funds
  (California, New Jersey, New York, Ohio, Pennsylvania)
Tax-Exempt Money Market Fund
Treasury Money Market Fund

VARIABLE  ANNUITY PLAN
- --------------------------------------------------------------------------------
Balanced Portfolio
Diversified Value Portfolio
Equity Income Portfolio
Equity Index Portfolio
Growth Portfolio
High-Grade Bond Portfolio
High Yield Bond Portfolio
International Portfolio
Mid-Cap Index Portfolio
Money Market Portfolio
REIT Index Portfolio
Short-Term Corporate Portfolio
Small Company Growth Portfolio

*Offers Institutional Shares.

 For information about Vanguard funds, including charges and expenses, obtain a
prospectus from The Vanguard Group, P.O. Box 2600, Valley Forge, PA 19482-2600.
               Read it carefully before you invest or send money.
<PAGE>
- --------------------------------------------------------------------------------
THE PEOPLE WHO GOVERN YOUR FUND
The  Trustees of your mutual fund are there to see that the fund is operated and
managed in your best interests  since,  as a shareholder,  you are part owner of
the fund.  Your  fund  Trustees  also  serve on the  Board of  Directors  of The
Vanguard  Group,  which is owned by the  funds  and  exists  solely  to  provide
services to them on an at-cost basis.
     Seven of Vanguard's nine board members are  independent,  meaning that they
have no  affiliation  with  Vanguard or the funds they  oversee,  apart from the
sizable personal investments they have made as private  individuals.  They bring
distinguished  backgrounds  in business,  academia,  and public service to their
task of working with Vanguard officers to establish the policies and oversee the
activities of the funds.
     Among board members' responsibilities are selecting investment advisers for
the  funds;  monitoring  fund  operations,  performance,  and  costs;  reviewing
contracts;  nominating  and  selecting  new  Trustees/Directors;   and  electing
Vanguard officers.
     The list below provides a brief description of each Trustee's  professional
affiliations.  Noted in  parentheses is the year in which the Trustee joined the
Vanguard Board.
- --------------------------------------------------------------------------------
TRUSTEES
JOHN C. BOGLE (1967) Founder, Senior Chairman of the Board, and Director/Trustee
of The  Vanguard  Group,  Inc.,  and  each of the  investment  companies  in The
Vanguard Group.

JOHN J. BRENNAN  (1987)  Chairman of the Board,  Chief  Executive  Officer,  and
Director/Trustee  of The  Vanguard  Group,  Inc.,  and  each  of the  investment
companies in The Vanguard Group.

JOANN HEFFERNAN HEISEN (1998) Vice President,  Chief Information  Officer, and a
member of the  Executive  Committee of Johnson & Johnson;  Director of Johnson &
JohnsonoMerck Consumer Pharmaceuticals Co., The Medical Center at Princeton, and
Women's Research and Education Institute.

BRUCE K.  MACLAURY  (1990)  President  Emeritus  of The  Brookings  Institution;
Director of  American  Express  Bank Ltd.,  The St. Paul  Companies,  Inc.,  and
National Steel Corp.

BURTON G. MALKIEL  (1977)  Chemical  Bank  Chairman's  Professor  of  Economics,
Princeton  University;  Director of Prudential  Insurance Co. of America,  Banco
Bilbao Gestinova,  Baker Fentress & Co., The Jeffrey Co., and Select Sector SPDR
Trust.

ALFRED M. RANKIN, JR. (1993) Chairman, President, and Chief Executive Officer of
NACCO Industries,  Inc.;  Director of NACCO Industries,  The BFGoodrich Co., and
The Standard Products Co.

JOHN C.  SAWHILL  (1991)  President  and Chief  Executive  Officer of The Nature
Conservancy;  formerly,  Director  and  Senior  Partner  of  McKinsey  & Co. and
President  of New York  University;  Director of Pacific Gas and  Electric  Co.,
Procter & Gamble Co., NACCO Industries, and Newfield Exploration Co.

JAMES O. WELCH,  JR. (1971) Retired  Chairman of Nabisco Brands,  Inc.;  retired
Vice Chairman and Director of RJR Nabisco;  Director of TECO Energy,  Inc.,  and
Kmart Corp.

J.  LAWRENCE  WILSON  (1985)  Retired  Chairman of Rohm & Haas Co.;  Director of
Cummins Engine Co. and The Mead Corp.; Trustee of Vanderbilt University.

OTHER FUND OFFICERS
RAYMOND J. KLAPINSKY Secretary;  Managing Director and Secretary of The Vanguard
Group,  Inc.;  Secretary  of each of the  investment  companies  in The Vanguard
Group.

THOMAS J. HIGGINS Treasurer; Principal of The Vanguard Group, Inc.; Treasurer of
each of the investment companies in The Vanguard Group.

VANGUARD MANAGING DIRECTORS

R. GREGORY BARTON o Legal Department.
ROBERT A. DISTEFANO o Information Technology.
JAMES H. GATELY o Individual Investor Group.
KATHLEEN C. GUBANICH o Human Resources.
IAN A. MACKINNON o Fixed Income Group.
F. WILLIAM MCNABB, III o Institutional Investor Group.
MICHAEL S. MILLER o Planning and Development.
RALPH K. PACKARD o Chief Financial Officer.
GEORGE U. SAUTER o Core Management Group.
<PAGE>
ABOUT OUR COVER
Our cover art,  depicting HMS Vanguard at sea, is a
reproduction  of Leading the Way, a 1984 work created and
copyrighted by noted naval artist Tom Freeman,
of Forest Hill, Maryland.

All comparative mutual fund data are from Lipper Inc. or Morningstar,
Inc., unless otherwise noted.

"Standard & Poor's(R),"  "S&P(R),"  "S&P  500(R),"  "Standard & Poor's 500,"
and "500" are trademarks of The McGraw-Hill Companies, Inc.

Frank Russell Company is the owner of trademarks and copyrights
relating to the Russell Indexes.  "Wilshire 4500" and "Wilshire 5000"
are trademarks of Wilshire Associates.

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This report is intended for the fund's
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is preceded or  accompanied by the
current fund prospectus.

Q730-12/09/1999
(C) 1999 The Vanguard Group, Inc.
All rights reserved.
Vanguard Marketing
Corporation, Distributor.


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