PREFERRED INCOME OPPORTUNITY FUND INC
N-30D, 1999-01-27
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<PAGE>
PREFERRED INCOME OPPORTUNITY FUND
INCORPORATED

Dear Shareholder:
 
     Fiscal 1998 ending on November 30th was a good year. Not great, but good!
The Preferred Income Opportunity Fund earned a return of 8.3% on the net asset
value ("NAV") of its shares despite market conditions that tried our patience at
times.
 
     The following table presents our "report card" on the performance of the
Fund over the last one, three and five years. For perspective, we have also
included in the table the returns on a composite of over 50 higher quality
closed-end bond funds, which typically have investment objectives similar to
those of the Fund. We hope to earn our keep by doing better than the bond funds
over longer holding periods, including both ups and downs in interest rates. In
any single year, however, the impact of interest rate trends on our hedging
strategy will probably have the greatest effect on how we compare to the bond
funds.

- ------------------------------------------------------------------------------- 

                   TOTAL RETURN PER YEAR ON NET ASSET VALUE*
                           FOR PERIODS ENDED 11/30/98
 
<TABLE>
<CAPTION>
                                                         ONE     THREE    FIVE
                                                         YEAR    YEARS    YEARS
                                                         ----    -----    -----
<S>                                                      <C>     <C>      <C>
Preferred Income Opportunity Fund......................  8.0%    11.4%    10.6%
Lipper Higher Quality Bond Fund Composite**............  7.5%     8.0%     7.2%

Source: Lipper Inc.

 * Distributions are assumed to be reinvested at NAV in accordance with Lipper's
   practice, which differs from the procedures used elsewhere in this report.
** Includes all U.S. Government bond, mortgage bond and term trust, and
   investment grade bond funds in Lipper's closed-end fund database.
</TABLE>

- ------------------------------------------------------------------------------- 

     As shown by the table, the Fund's total return on NAV has substantially
outperformed the bond fund composite over the last three years and five years.
For example, the Fund's return of 10.6% per year over five years compares to an
average of 7.2% for the bond funds. In contrast, the return in the last year did
not really distinguish the Fund very much from the composite. Actually, this
rather bland picture of the last year was the net result of considerably more
dramatic, but offsetting, market events.
 
     Economic distress in Asia, Russia and parts of Latin America generally
dominated financial markets in the past year. A "flight to quality" resulted,
reaching near panic this last fall, as investors seeking safety drove up the
prices of U.S. Treasury bonds and reduced the yield on long-term Treasuries by

<PAGE>
approximately a full percentage point. Other fixed income markets, particularly
junk bonds and emerging market debt, lagged far behind and, in some cases,
actually declined in value. Better quality preferreds, such as those in which
the Fund invests, walked the line between the two extremes. The serious problems
suffered by a few highly visible "hedge funds" demonstrated how treacherous
these conflicting trends could be.
 
     On the surface, our hedges worked very well in Fiscal 1998. The
appreciation on our portfolio of preferreds offset the losses on our hedges with
a little to spare. However, this came about because our use of purchased put
options kept hedge losses down to manageable levels, not because the
appreciation on our preferreds was all that big. Had the preferred market
performed as well as the Treasury bond market, the Fund would have enjoyed a
really great year. We believe the preferred market is generally undervalued as a
result of these trends, but we are very cautious about predicting when
preferreds might come back into line with Treasuries.
 
     Fortunately, we have had some good opportunities to add to the Fund's
performance by moving money around within the preferred market. Traditional
preferreds eligible for the Dividends Received Deduction ("DRD") available to
corporate investors were the best performers in the preferred market earlier in
the fiscal year, while hybrid preferreds saved their best for last. This gave us
the opportunity to move more than 20% of the Fund's portfolio from some more
fully valued traditional preferreds into undervalued hybrids before hybrids
started to shine. Revolving door investment opportunities like this make a
portfolio manager's day!
 
                 [PREFERRED INCOME OPPORTUNITY FUND PIE CHART]

<TABLE>
<CAPTION>           
                                           11/30/97          11/30/98       
     <S>                                   <C>               <C>

     Adjustable Rates                       24.3%             13.8%
     Traditional Fixed Rates                46.7%             36.9%  
     Common Stock                            4.7%              1.4%  
     Non-DRD Preferreds & Securities        22.2%             43.5%
      (Hybrids)
     Cash and Other                          2.1%              4.4% 
</TABLE>                    
 
     The pie charts vividly illustrate the shift from traditional fixed and
adjustable rate preferreds into hybrid preferreds that took place over the
course of the year. Although the small position in common stocks almost slips
below the radar screen, the Fund did benefit from our ventures during the year
in several common stocks. Typically, these instances involved utilities whose
common shares clearly seemed to offer better investment opportunities than their
preferred stocks in which the Fund might otherwise have invested.


 
                                        2

<PAGE>
     The Fund's income was one of the high points of Fiscal 1998. Despite the
decline in interest rates, the Fund maintained a constant dividend rate of
$0.068 per share throughout the year. In part, this was due to the increase in
our holdings of hybrid preferreds, which yield considerably more than
traditional preferreds. The special distribution of $0.81 per share payable
December 31, 1998, primarily representing capital gains realized by the Fund,
will reduce the Fund's earning assets and necessitate lowering the monthly
dividend rate per share to $0.0655 per share effective January 29, 1999. As
illustrated in the Question and Answer section following this letter, we do not
anticipate that shareholders who reinvest the year-end distribution through the
Fund's Dividend Reinvestment Plan will see much change in their total dividend
income.
 
     The Question and Answer section that follows provides additional important
information on the Fund's accomplishments and operations. It is definitely
"recommended reading"!

                                         Sincerely yours,
 
                                         /s/ Robert T. Flaherty
 
                                         Robert T. Flaherty
                                         Chairman of the Board
 
December 22, 1998
 


                                        3

<PAGE>
 
                             QUESTIONS AND ANSWERS
 
HOW HAS THE FUND'S INCOME BEEN AFFECTED BY CHANGES IN INTEREST RATES?
 
     The following chart is one of our favorites. It sends a very simple message
about a very complicated strategy.
 

    [30 YEAR TREASURY YIELD CHART]                 [MONTHLY DIVIDEND INCOME]
                        
Feb-92    7.79          Aug-95    6.61       Feb-92              Aug-95    83.83
Mar-92    8.03          Sep-95    6.5        Mar-92              Sep-95    83.83
Apr-92    7.84          Oct-95    6.36       Apr-92              Oct-95    83.83
May-92    7.84          Nov-95    6.08       Mar-92    82.5      Nov-95    83.83
Jun-92    7.78          Dec-95    5.95       Jun-92    82.5      Dec-95    78.73
Jul-92    7.46          Jan-96    6.05       Jul-92    82.5      Jan-96    78.73
Aug-92    7.41          Feb-96    6.36       Aug-92    82.5      Feb-96    78.73
Sep-92    7.38          Mar-96    6.67       Sep-92    82.5      Mar-96    78.73
Oct-92    7.62          Apr-96    6.83       Oct-92    82.5      Apr-96    78.73
Nov-92    7.6           May-96    7          Nov-92    82.5      May-96    83.83
Dec-92    7.39          Jun-96    6.95       Dec-92    83.14     Jun-96    83.83
Jan-93    7.19          Jul-96    7.01       Jan-93    83.14     Jul-96    83.83
Feb-93    6.9           Aug-96    7.12       Feb-93    83.14     Aug-96    83.83
Mar-93    6.92          Sep-96    6.9        Mar-93    83.14     Sep-96    83.83
Apr-93    6.93          Oct-96    6.81       Apr-93    83.14     Oct-96    83.83
May-93    6.98          Nov-96    6.51       May-93    83.14     Nov-96    83.83
Jun-93    6.67          Dec-96    6.6        Jun-93    83.14     Dec-96    84.06
Jul-93    6.56          Jan-97    6.79       Jul-93    83.14     Jan-97    84.06
Aug-93    6.09          Feb-97    6.8        Aug-93    83.14     Feb-97    84.06
Sep-93    6.02          Mar-97    7.09       Sep-93    83.14     Mar-97    84.06
Oct-93    5.97          Apr-97    6.89       Oct-93    83.14     Apr-97    84.06
Nov-93    6.3           May-97    6.98       Nov-93    83.14     May-97    84.06
Dec-93    6.35          Jun-97    6.74       Dec-93    73.87     Jun-97    84.06
Jan-94    6.24          Jul-97    6.45       Jan-94    79.87     Jul-97    84.06
Feb-94    6.66          Aug-97    6.61       Feb-94    79.87     Aug-97    84.06
Mar-94    7.09          Sep-97    6.3        Mar-94    79.87     Sep-97    84.06
Apr-94    7.26          Oct-97    6.15       Apr-94    79.87     Oct-97    84.06
May-94    7.34          Nov-97    6.04       May-94    85.89     Nov-97    84.06
Jun-94    7.61          Dec-97    5.95       Jun-94    85.89     Dec-97    79.79
Jul-94    7.39          Jan-98    5.9        Jul-94    85.89     Jan-98    79.79
Aug-94    7.48          Feb-98    6.02       Aug-94    85.89     Feb-98    79.79
Sep-94    7.82          Mar-98    5.93       Sep-94    85.89     Mar-98    79.79
Oct-94    7.96          Apr-98    5.95       Oct-94    85.89     Apr-98    79.79
Nov-94    7.94          May-98    5.8        Nov-94    89.17     May-98    79.79
Dec-94    7.88          Jun-98    5.62       Dec-94    88.36     Jun-98    79.79
Jan-95    7.73          Jul-98    5.72       Jan-95    88.36     Jul-98    79.79
Feb-95    7.55          Aug-98    5.26       Feb-95    88.36     Aug-98    79.79
Mar-95    7.43          Sep-98    4.98       Mar-95    88.36     Sep-98    79.79
Apr-95    7.33          Oct-98    5.15       Apr-95    88.36     Oct-98    79.79
May-95    6.63          Nov-98    5.07       May-95    88.36     Nov-98    79.79
Jun-95    6.54          Dec-98               Jun-95    83.83     Dec-98    81.37
Jul-95    6.9           Jan-99               Jul-95    83.83     Jan-99    81.37

 
     The Fund's income (shown by the solid line) has generally managed to hold
up pretty well when the interest rate on long term Treasury bonds (the dotted
line) has gone down. In contrast, when the Treasury interest rate has increased,
income from the Fund has shared in the increase. Over the life of the Fund,
income has generally moved sideways, with a few bumps here and there, despite a
substantial decline in interest rates (shown on the right hand scale). This is
the way the Fund was designed to work.
 
     The chart is based on a hypothetical investment in 1,000 shares of the Fund
at its inception. It assumes that the regular monthly dividends were taken in
cash and that additional shares were acquired only by reinvesting the portion of
each special year-end distribution that was above and beyond the regular monthly
dividend. We have also projected the impact of the special distribution payable
on December 31, 1998 and the new dividend rate effective in January.



                                        4

<PAGE>
WHAT ABOUT TOTAL RETURN INCLUDING CHANGES IN NAV? HOW HAS IT RESPONDED TO
CHANGES IN INTEREST RATES?
 
     A great strength of the Preferred Income Opportunity Fund has been its
ability to do well in down markets. The following bar chart compares the Fund's
total return since inception, including both income and changes in net asset
value, to the average returns on the Lipper composite of higher quality closed-
end bond funds. The historical returns are also broken down between strong and
weak markets based upon whether the bond fund composite, on a month by month
basis, managed to beat the total return on Treasury bills.

                       PREFERRED INCOME OPPORTUNITY FUND
 
<TABLE>
<CAPTION>
                           Lipper Index                   PFO
<S>                        <C>                          <C>
Weak Markets                   -8.8                      -0.8
Strong Markets                 18.30                     19.90
All Markets                     7.90                     12.20
</TABLE>

THE DATA, PREPARED BY LIPPER INC, SHOW THE AVERAGE ANNUALIZED TOTAL RETURNS IN 
THE 82 MONTHS ENDED 11/30/98, INCLUDING 29 WEAK MARKETS AND 53 STRONG MARKETS.
 
     Naturally, the Fund produced its biggest returns in strong markets
characterized by declining interest rates and rising prices for bonds and
preferreds. In these good times, it had a clear edge over the bond funds, which
also did well. In weak markets, typically caused by rising interest rates that
drove down bond and preferred prices, the Fund distinguished itself by almost
breaking even when the average return on the bond funds was down significantly.
Doing reasonably well in good times and not giving it back in bad times has
produced outstanding returns for the Fund over its entire history.
 
     This part may not be as obvious. The same strategies that supported the
Fund's income, as described in the preceding Q&A, were also responsible for the
strong showing of the Fund's total return. These include the combination of
hedging and leverage that is unique to the Fund and its sister funds. If income
does well, it is a pretty good bet that total return will also do well.


 
                                        5

<PAGE>
HOW DOES THE MARKET PRICE OF THE FUND'S SHARES COMPARE TO THEIR NET ASSET VALUE?
 
     As illustrated by the following chart, the Fund's shares are selling in the
market at a moderate discount from net asset value. For the last two years, that
discount has stayed within a relatively narrow range, and the returns on the
market value of the shares have mirrored those on the net asset value rather
closely.

                   [PREFERRED INCOME OPPORTUNITY FUND GRAPH]
                    PREMIUM/DISCOUNT OF MARKET PRICE TO NAV

<TABLE>

<S>        <C>         <C>        <C>         <C>        <C>         <C>        <C>         <C>        <C>         <C>        <C>
2/21/92      7.26      4/9/93       5.78      5/27/94     -3.12      7/14/95     -7.64      8/30/96     -8.36      10/17/97    -5.06
2/28/92      8.05      4/16/93      5.70      6/3/94      -6.83      7/21/95    -10.87      9/6/96      -8.36      10/24/97    -5.27
3/6/92       8.74      4/23/93      6.59      6/10/94     -2.88      7/28/95     -9.11      9/13/96     -6.61      10/31/97    -4.77
3/13/92      9.80      4/30/93      6.51      6/17/94     -4.57      8/4/95      -9.73      9/20/96     -9.91      11/7/97     -4.42
3/20/92      8.19      5/7/93       5.13      6/24/94     -3.93      8/11/95    -10.18      9/27/96     -9.91      11/14/97    -3.77
3/27/92      5.56      5/14/93      6.10      7/1/94      -4.09      8/18/95    -10.11      10/4/96     -8.76      11/21/97    -6.41
4/3/92       5.38      5/21/93      5.70      7/8/94      -3.44      8/25/95     -7.80      10/11/96    -8.76      11/28/97    -5.76
4/10/92      7.05      5/28/93      4.41      7/15/94     -4.90      9/1/95      -7.06      10/18/96    -9.35      12/5/97     -4.98
4/17/92      5.47      6/4/93       4.97      7/22/94     -2.94      9/8/95      -8.33      10/25/96    -8.34      12/12/97    -4.69
4/24/92      5.90      6/11/93      5.61      7/29/94     -3.27      9/15/95     -8.13      11/1/96     -7.96      12/19/97    -6.48
5/1/92       5.46      6/18/93      4.97      8/5/94      -2.21      9/22/95     -7.49      11/8/96     -9.32      12/26/97    -5.02
5/8/92       5.36      6/25/93      4.17      8/12/94     -2.98      9/29/95     -6.41      11/15/96    -6.30      1/2/98      -1.71
5/15/92      3.06      7/2/93       4.72      8/19/94     -3.76      10/6/95     -7.18      11/22/96    -5.86      1/9/98      -1.97
5/22/92      2.48      7/9/93       4.25      8/26/94     -2.94      10/13/95   -10.06      11/29/96    -6.08      1/16/98     -1.85
5/29/92      3.07      7/16/93      3.62      9/2/94      -2.04      10/20/95    -9.09      12/6/96     -7.92      1/23/98     -6.20
6/5/92       2.82      7/23/93      1.63      9/9/94      -3.18      10/27/95   -10.12      12/13/96    -8.13      1/30/98     -4.77
6/12/92      4.00      7/30/93      3.06      9/16/94     -4.09      11/3/95    -12.32      12/20/96   -10.09      2/6/98      -5.30
6/19/92      3.57      8/6/93       2.12      9/23/94     -6.28      11/10/95   -11.15      12/27/96    -8.37      2/13/98     -6.04
6/26/92      4.42      8/13/93      1.81      9/30/94     -5.10      11/17/95   -10.71      1/3/97      -6.93      2/20/98     -3.63
7/3/92       4.75      8/20/93      0.08      10/7/94    -13.22      11/24/95    -9.91      1/10/97     -5.62      2/27/98     -4.77
7/10/92      6.26      8/27/93      3.70      10/14/94   -13.68      12/1/95    -10.14      1/17/97     -6.93      3/6/98      -4.27
7/17/92      8.00      9/3/93       3.31      10/21/94    -14.1      12/8/95    -11.74      1/24/97     -8.34      3/13/98     -5.68
7/24/92      5.92      9/10/93      4.01      10/28/94    -10.4      12/15/95   -12.33      1/31/97     -6.78      3/20/98     -4.87
7/31/92      6.47      9/17/93      3.38      11/4/94     -7.86      12/22/95   -12.65      2/7/97      -6.23      3/27/98     -5.79
8/7/92       6.13      9/24/93      2.44      11/11/94   -10.87      12/29/95   -14.54      2/14/97     -5.51      4/3/98      -6.82
8/14/92      6.28      10/1/93      2.14      11/18/94    -9.90      1/5/96     -11.97      2/21/97     -6.45      4/10/98     -5.08
8/21/92      5.14      10/8/93      2.61      11/23/94    -7.70      1/12/96    -12.79      2/28/97     -6.05      4/17/98     -6.20
8/28/92      5.39      10/15/93     2.63      12/2/94     -4.02      1/19/96    -13.12      3/7/97      -5.81      4/24/98     -7.68
9/4/92       5.06      10/22/93     2.46      12/9/94     -8.68      1/26/96    -11.46      3/14/97     -6.54      5/1/98      -6.18
9/11/92      6.84      10/29/93     0.90      12/16/94    -7.32      2/2/96     -12.33      3/21/97     -7.15      5/8/98      -5.40
9/18/92      4.74      11/5/93      0.00      12/23/94    -6.04      2/9/96     -12.33      3/28/97     -7.15      5/15/98     -7.17
9/25/92      4.41      11/12/93    -1.07      12/30/94    -8.51      2/16/96    -12.79      4/4/97      -5.73      5/22/98     -7.10
10/2/92      6.20      11/19/93    -2.82      1/6/95      -0.10      2/23/96    -13.03      4/11/97     -7.77      5/29/98     -6.48
10/9/92      6.75      11/26/93    -1.79      1/13/95     -1.41      3/1/96     -11.24      4/18/97     -9.04      6/5/98      -6.43
10/16/92     4.90      12/3/93     -0.76      1/20/95     -4.21      3/8/96     -14.65      4/25/97     -7.48      6/12/98     -6.27
10/23/92     1.88      12/10/93    -3.34      1/27/95     -6.19      3/15/96    -15.08      5/2/97      -6.72      6/19/98     -5.73
10/30/92     2.78      12/17/93    -3.38      2/3/95      -2.34      3/22/96    -14.87      5/9/97      -6.18      6/26/98     -6.00
11/6/92      1.80      12/24/93    -4.31      2/10/95     -3.14      3/29/96    -15.15      5/16/97     -6.47      7/3/98      -5.75
11/13/92     1.88      12/31/93    -1.53      2/17/95     -5.88      4/5/96     -13.15      5/23/97     -5.73      7/10/98     -5.61
11/20/92     4.08      1/7/94      -0.36      2/24/95     -3.76      4/12/96    -12.86      5/30/97     -3.62      7/17/98     -5.18
11/27/92     8.44      1/14/94      1.57      3/3/95      -2.97      4/19/96    -12.79      6/6/97      -6.15      7/24/98     -6.93
12/4/92      6.30      1/21/94     -1.29      3/10/95     -5.85      4/26/96    -13.83      6/13/97     -4.81      7/31/98     -5.26
12/11/92     6.13      1/28/94     -3.77      3/17/95     -5.23      5/3/96     -11.53      6/20/97     -4.73      8/7/98      -4.72
12/18/92     6.91      2/4/94      -3.19      3/24/95     -5.34      5/10/96    -11.30      6/27/97     -4.18      8/14/98     -8.64
12/25/92     5.36      2/11/94     -4.62      3/31/95     -3.93      5/17/96    -14.08      7/4/97      -4.98      8/21/98     -8.63
1/1/93       6.21      2/18/94     -8.63      4/7/95      -3.41      5/24/96    -13.86      7/11/97     -5.85      8/28/98     -5.40
1/8/93       6.79      2/25/94     -5.00      4/14/95     -3.93      5/31/96    -13.86      7/18/97     -4.86      9/4/98      -6.18
1/15/93      5.95      3/4/94      -3.92      4/21/95     -6.90      6/7/96     -12.55      7/25/97     -6.30      9/11/98     -4.87
1/22/93      4.34      3/11/94     -3.15      4/28/95     -3.41      6/14/96    -13.37      8/1/97      -2.73      9/18/98     -3.92
1/29/93      5.76      3/18/94     -5.85      5/5/95      -5.76      6/21/96    -13.01      8/8/97      -7.01      9/25/98     -4.02
2/5/93       4.83      3/25/94     -5.62      5/12/95     -3.93      6/28/96     -9.18      8/15/97     -8.09      10/2/98     -5.54
2/12/93      2.84      4/1/94      -5.52      5/19/95     -9.33      7/5/96     -10.79      8/22/97     -7.67      10/9/98     -6.51
2/19/93      2.02      4/8/94      -5.10      5/26/95     -7.53      7/12/96    -10.13      8/29/97     -4.72      10/16/98    -4.85
2/26/93      3.10      4/15/94     -9.76      6/2/95      -4.81      7/19/96    -11.22      9/5/97      -5.80      10/23/98    -4.06
3/5/93       4.73      4/22/94    -10.12      6/9/95      -7.29      7/26/96     -9.39      9/12/97     -6.56      10/30/98    -6.16
3/12/93      6.51      4/29/94    -10.42      6/16/95     -8.07      8/2/96      -8.76      9/19/97     -5.10      11/6/98     -3.96
3/19/93      3.03      5/6/94      -7.75      6/23/95     -7.49      8/9/96      -6.88      9/26/97     -4.92      11/13/98    -4.81
3/26/93      4.57      5/13/94     -7.37      6/30/95     -6.86      8/16/96     -6.73      10/3/97     -2.92      11/20/98    -6.41
4/2/93       5.14      5/20/94     -6.36      7/7/95      -6.90      8/23/96     -7.79      10/10/97    -4.92      11/27/98    -4.78
</TABLE>
 
 
DOES THE FUND HAVE A YEAR 2000 PROBLEM?
 
     By now, everyone has probably heard about the so-called "Y2K" problem. This
has resulted from too many short cuts taken by computer programmers over the
years, which may cause some systems that are important to our daily lives not
being able to determine that the year 2000 is not really 1900. There is clearly
a significant risk that some systems will fail and cause a chain reaction
affecting other users that depend upon them.
 
     The Fund could suffer interruptions and other material adverse effects
unless the Year 2000 problem is solved properly, not only by the Fund, but also
by others such as our suppliers and service providers, the financial markets in
which Funds operates, and the companies in which we invest. The Fund is taking
what it considers to be reasonable steps to deal with this exposure, but there
are no assurances that the Fund will not be affected by the Y2K problem.

 
                                        6

<PAGE>
- --------------------------------------------------------------------------------
                                  Preferred Income Opportunity Fund Incorporated
                                                                  FINANCIAL DATA
                                           PER SHARE OF COMMON STOCK (UNAUDITED)
                             ---------------------------------------------------
 
<TABLE>
<CAPTION>
                                                                      DIVIDEND
                             DIVIDEND   NET ASSET       NYSE        REINVESTMENT
                               PAID       VALUE     CLOSING PRICE     PRICE(1)
                             --------   ---------   -------------   ------------
<S>                          <C>        <C>         <C>             <C>
December 31, 1997..........   $0.325     $13.46       $13.0000         $13.40
January 31, 1998...........    0.068      13.52        12.8750          12.95
February 28, 1998..........    0.068      13.52        12.8750          12.96
March 31, 1998.............    0.068      13.62        12.8125          12.92
April 30, 1998.............    0.068      13.59        12.6250          12.75
May 31, 1998...............    0.068      13.70        12.8125          12.92
June 30, 1998..............    0.068      13.80        13.1250          13.11
July 31, 1998..............    0.068      13.59        12.8750          12.86
August 31, 1998............    0.068      13.64        12.8750          12.92
September 30, 1998.........    0.068      13.54        12.8125          12.81
October 31, 1998...........    0.068      13.32        12.5000          12.59
November 30, 1998..........    0.068      13.50        12.8750          12.95
</TABLE>
 
- ---------------
(1) See ADDITIONAL INFORMATION; Dividend Reinvestment and Cash Purchase Plan on
    pages 25 and 26 of this report.




                                        7

<PAGE>
- --------------------------------------------------------------------------------
Preferred Income Opportunity Fund Incorporated
PORTFOLIO OF INVESTMENTS
NOVEMBER 30, 1998
- ---------------------------------------------------------------
 
<TABLE>
<CAPTION>
                                                   VALUE
SHARES/PAR                                        (NOTE 1)
- ----------                                      ------------
<C>          <S>                                <C>
 PREFERRED STOCKS AND SECURITIES -- 94.2%
  ADJUSTABLE RATE PREFERRED STOCKS -- 13.8%
        UTILITIES -- 7.6%
   22,470    Arizona Public Service Company,
               Series Q, Adj. Rate Pfd. ......  $  2,235,765
  264,504    New York State Electric & Gas
               Corporation,
               Series B, Adj. Rate Pfd. ......     6,215,844
             Niagara Mohawk Power Corporation:
   95,275      Series A, Adj. Rate Pfd. ......     2,432,490
  190,320      Series B, Adj. Rate Pfd. ......     4,841,265
   25,000      Series C, Adj. Rate Pfd. ......       635,938
    6,800    Northern Indiana Public Service
               Company,
               Series A, Adj. Rate Pfd. ......       343,400
                                                ------------
             TOTAL UTILITY ADJUSTABLE RATE
               PREFERRED STOCKS...............    16,704,702
                                                ------------
        BANKING -- 6.2%
             Bank One Corporation:
    9,011      Series B, Adj. Rate Pfd. ......       906,732
   20,000      Series C, Adj. Rate Pfd. ......     2,012,500
             Bankers Trust New York
               Corporation:
  101,900      Series Q, Adj. Rate Pfd. ......     2,420,125
  151,700      Series R, Adj. Rate Pfd. ......     3,640,800
             Chase Manhattan Corporation:
   24,650      Series L, Adj. Rate Pfd. ......     2,378,725
   10,000      Series N, Adj. Rate Pfd. ......       222,500
   25,000    Citigroup Inc., Series R, Adj.
               Rate Pfd. .....................       561,719
    3,200    Morgan (J.P.) & Company Inc.,
               Series A, Adj. Rate Pfd. ......       288,000
    7,600    Republic New York Corporation,
               Series D, Adj. Rate Pfd. ......       190,000
   22,700    Wells Fargo & Company,
               Series B, Adj. Rate Pfd. ......     1,139,256
                                                ------------
             TOTAL BANKING ADJUSTABLE RATE
               PREFERRED STOCKS...............    13,760,357
                                                ------------
             TOTAL ADJUSTABLE RATE PREFERRED
               STOCKS.........................    30,465,059
                                                ------------
</TABLE>
 
<TABLE>
<CAPTION>
                                                   VALUE
SHARES/PAR                                        (NOTE 1)
- ----------                                      ------------
<C>          <S>                                <C>
  FIXED RATE PREFERRED STOCKS AND SECURITIES -- 80.4%
        UTILITIES -- 34.2%
             Alabama Power & Company:
    3,332      4.60% Pfd. ....................  $    302,379
    1,852      4.72% Pfd. ....................       172,467
      100      4.92% Pfd. ....................         9,712
    7,250      5.20% Pfd. ....................       185,781
   80,000    Alabama Power Capital Trust II,
               7.60% TOPrS....................     2,075,000
   28,100    Alabama Power Capital Trust I,
               7.375% TOPrS...................       721,819
   60,400    Appalachian Power Company,
               8.00% QUIDS, Series B..........     1,566,625
   22,646    Arizona Public Service Company
               7.25% Pfd., Series W...........       566,150
             Baltimore Gas & Electric Company:
   10,650      6.70% Pfd., Series 1993........     1,214,100
   27,200      6.99% Pfd., Series 1995........     3,219,800
   10,000    Boston Edison Company,
               4.78% Pfd......................       940,000
    1,328    Central Hudson Gas & Electric
               Corporation,
               4.35% Pfd., Series D...........       112,050
   27,000    Columbus Southern Power Company,
               7.92% Jr. Sub. Debt,
               Series B.......................       696,938
    7,500    Commonwealth Edison Company,
               $8.40 Pfd. ....................       770,625
   29,000    Consolidated Edison Company
               of New York,
               7.75% QUICS, Series A..........       744,937
  134,100    CPL Capital,
               8.00% QUIPS, Series A..........     3,511,744
             Duke Energy Corporation:
    7,019      4.50% Pfd., Series C...........       622,936
   10,003      7.85% Pfd., Series S...........     1,161,598
    1,009      7.00% Pfd., Series W...........       114,521
             Duquesne Light Company:
   20,000      7.375% QIB, Series E...........       501,250
   53,750      Duquesne Capital,
               8.375% MIPS, Series A..........     1,387,422
    5,050    El Paso Tennessee Pipeline
               Company, 8.25% Pfd.,
               Series A.......................       278,381
</TABLE>
 
                       See Notes to Financial Statements.


                                        8

<PAGE>
- --------------------------------------------------------------------------------
                                  Preferred Income Opportunity Fund Incorporated
                                            PORTFOLIO OF INVESTMENTS (CONTINUED)
                                                               NOVEMBER 30, 1998
                 ---------------------------------------------------------------
 
<TABLE>
<CAPTION>
                                                   VALUE
SHARES/PAR                                        (NOTE 1)
- ----------                                        --------
<C>          <S>                                <C>
PREFERRED STOCKS AND SECURITIES (CONTINUED)
      FIXED RATE PREFERRED STOCKS AND SECURITIES (CONTINUED)
        UTILITIES (CONTINUED)
             Florida Power & Light Company:
    4,000      4.50% Pfd. ....................  $    361,500
    4,105      4.35% Pfd., Series E...........       352,004
   32,850      6.98% Pfd., Series S...........     3,720,262
   14,200      7.05% Pfd., Series T...........     1,625,900
             Georgia Power Company:
    1,246      $6.48 Pfd. ....................       130,519
    3,481      $6.60 Pfd. ....................       364,635
   13,500    Capital Trust III,
               7.75%, Series V................       351,844
    4,500    Gulf Power Company,
               7.625% QUIPS, Series A.........       116,719
             Hawaiian Electric Company, Inc.:
   23,600      HECO Capital Trust I,
               8.05% QUIPS....................       612,125
   23,500      Hawaiian Electric Industries
               Capital Trust I,
               8.36% TOPrS....................       618,344
   45,241    HL&P Capital Trust I,
               8.125%, Series A Security......     1,173,438
             Indiana Michigan Power Company:
   10,000      8.00% Pfd., Series A...........       259,375
   20,000      7.60% Pfd., Series B...........       511,250
    6,750    Indianapolis Power & Light
               Company, 5.65% Pfd.............       749,250
    8,845    Jersey Central Power & Light
               Company,
               7.52% Sinking Fund Pfd.,
               Series K.......................       925,408
   22,000    MidAmerican Energy Financing I,
               7.98% QUIPS, Series A..........       567,875
   15,000    Mississippi Power Company,
               6.32% Pfd. ....................       386,250
             Monongahela Power Company:
   24,000      8.00% QUIDS, Series A..........       616,500
   20,000      $7.73 Pfd., Series L...........     2,367,500
   10,000    MP&L Capital,
               8.05% QUIPS....................       259,375
    5,000    New York State Electric & Gas
               Corporation,
               6.30% Sinking Fund Pfd. .......       519,063
</TABLE>
 
<TABLE>
<CAPTION>
                                                   VALUE
SHARES/PAR                                        (NOTE 1)
- ----------                                        --------
<C>          <S>                                <C>
             Niagara Mohawk Power Corporation:
    6,250      4.10% Pfd. ....................  $    432,812
   26,802      7.85% Sinking Fund Pfd. .......       681,776
   62,000      9.50% Pfd. ....................     1,639,125
             Northern States Power Company:
    2,480      $4.10 Pfd. ....................       200,570
    2,660      $4.16 Pfd. ....................       218,120
   75,000      NSP Financing I 7.875% TOPrS...     2,001,563
             Nevada Power Company:
   28,360    NVP Capital I
               8.20% QUIPS, Series A..........       742,678
   53,000    NVP Capital III 7.75% TIPS.......     1,341,563
             Ohio Power Company:
   75,800      7.375% Sr. Note................     1,928,162
   47,500      7.92% QUIDS, Series B..........     1,220,156
    2,150    Pacific Enterprises,
               $4.50 Pfd. ....................       185,706
    2,493    Potomac Electric Power Company,
               $2.44 Pfd., Series 1957........       118,106
             Pennsylvania Power & Light
               Company:
   96,900    PP&L Capital Trust II,
               8.10% TOPrS....................     2,537,569
   30,400    PP&L Capital Trust,
               8.20% TOPrS....................       796,100
   49,000    PSCO Capital Trust,
               7.60% TOPrS....................     1,258,688
   12,350    PSI Energy, Inc.,
               6.875% Pfd. ...................     1,400,181
             Puget Sound Energy Inc.:
1,050,000    Puget Sound Capital Trust,
               8.231% 6/1/27 Capital Security,
               Series B.......................     1,162,875
   27,555      7.75% Sinking Fund Pfd. .......     2,900,164
  125,300      7.45% Pfd., Series II..........     3,633,700
    4,030    Rochester Gas & Electric
               Corporation, 4.75% Pfd.,
               Series I.......................       364,715
   46,500    San Diego Gas & Electric Company,
               6.80% Pfd. ....................     1,339,781
             South Carolina Electric & Gas:
   15,000      5.125% Purchase Fund Pfd. .....       735,000
  100,200    SCE&G Trust I,
               7.55%, Series A................     2,598,938
</TABLE>
 
                       See Notes to Financial Statements.



                                        9

<PAGE>
- --------------------------------------------------------------------------------
Preferred Income Opportunity Fund Incorporated
PORTFOLIO OF INVESTMENTS (CONTINUED)
NOVEMBER 30, 1998
- ---------------------------------------------------------------
 
<TABLE>
<CAPTION>
                                                   VALUE
SHARES/PAR                                        (NOTE 1)
- ----------                                        --------
<C>          <S>                                <C>
PREFERRED STOCKS AND SECURITIES (CONTINUED)
      FIXED RATE PREFERRED STOCKS AND SECURITIES (CONTINUED)
        UTILITIES (CONTINUED)
    4,000    Southern Indiana Gas & Electric,
               4.75% Pfd. ....................  $    372,000
   35,000    Southwestern Public Service
               Capital I, 7.85%, Series A.....       899,062
   57,300    Transcanada Capital,
               8.75% TOPrS....................     1,500,544
             Union Electric Power Company:
    3,000      $7.64 Pfd. ....................       351,000
4,000,000      7.69% 12/15/36 Capital
               Security, Series A.............     4,375,000
             Virginia Electric & Power
               Company:
    1,665      $4.04 Pfd. ....................       129,038
    2,270      $4.20 Pfd. ....................       183,019
    5,700      $6.98 Pfd. ....................       646,950
                                                ------------
             TOTAL UTILITY FIXED RATE
               PREFERRED STOCKS AND
               SECURITIES.....................    75,360,032
                                                ------------
        BANKING -- 18.3%
      500    ABN Amro North America,
               6.59% Pfd. 144A**..............       542,500
             BankAmerica Corporation:
2,650,000    BankAmerica Institutional,
               7.70% 12/31/26 Capital Security
               144A**.........................     2,871,937
   35,500    NB Capital Trust I,
               7.84% TOPrS....................       942,969
1,800,000      NB Capital Trust II, 7.83%
               12/15/26 Capital Security......     1,998,000
1,275,000    BankBoston Capital Trust II,
               7.75% 12/15/26 Capital
               Security, Series B.............     1,338,750
  540,000    Bank of New York, 7.78% 12/1/26
               Capital Security 144A**........       592,650
2,000,000    BT Capital Trust B,
               7.90% 1/15/27 Capital
               Security.......................     2,110,000
             Chase Manhattan Corporation:
  101,050      10.84% Pfd., Series C..........     3,025,184
1,300,000      Chase Capital I, 7.67% 12/1/26
               Capital Security, Series A.....     1,413,750
</TABLE>
 
<TABLE>
<CAPTION>
                                                   VALUE
SHARES/PAR                                        (NOTE 1)
- ----------                                        --------
<C>          <S>                                <C>
             Citigroup Inc.:
   20,000      6.365% Pfd., Series F..........  $  1,072,500
   10,000      6.213% Pfd., Series G..........       527,500
   50,780      6.231% Pfd., Series H..........     2,735,772
   48,300      5.864% Pfd., Series M..........     2,428,584
3,500,000    First Hawaiian Capital I,
               8.343% 7/1/27 Capital Security,
               Series B.......................     3,898,125
             First Union Corporation:
  300,000      First Union Institutional
               Capital I,
               8.04% 12/1/26 Capital
               Security.......................       339,000
1,885,000      First Union Institutional
               Capital II,
               7.85% 1/1/27 Capital
               Security.......................     2,089,994
   12,300    Fleet Financial Group, Inc.,
               6.75% Pfd., Series VI..........       694,950
2,500,000    Greenpoint Capital Trust I,
               9.10% 6/1/27 Capital
               Security.......................     2,681,250
2,900,000    JPM Capital Trust I,
               7.54% 1/15/27 Capital
               Security.......................     3,106,625
  500,000    Keycorp Institutional Capital,
               8.25% 12/15/26 Capital
               Security, Series B.............       577,500
      200    LaSalle National Corporation,
               6.46% Pfd. 144A**..............       214,500
             Republic New York Corporation:
    3,200      5.715% Pfd. ...................       164,400
4,785,000      Republic NY Capital Trust II,
               7.53% 12/4/26 Capital
               Security.......................     5,107,987
                                                ------------
             TOTAL BANKING FIXED RATE
               PREFERRED STOCKS AND
               SECURITIES.....................    40,474,427
                                                ------------
        FINANCIAL SERVICES -- 11.4%
             Bear Stearns Company:
   11,700    5.72% Pfd., Series F.............       548,437
   54,400    5.49% Pfd., Series G.............     2,454,800
2,500,000    Countrywide Capital III,
               8.05% 6/15/27 Capital Security,
               Series B.......................     2,731,250
   27,000    DLJ Capital Trust,
               8.42% Pfd. ....................       700,313
15,000...    Heller Financial,
               6.687% Pfd., Series C..........     1,501,875
</TABLE>
 
                       See Notes to Financial Statements.



                                       10

<PAGE>
- --------------------------------------------------------------------------------
                                  Preferred Income Opportunity Fund Incorporated
                                            PORTFOLIO OF INVESTMENTS (CONTINUED)
                                                               NOVEMBER 30, 1998
                 ---------------------------------------------------------------
 
<TABLE>
<CAPTION>
                                                   VALUE
SHARES/PAR                                        (NOTE 1)
- ----------                                        --------
<C>          <S>                                <C>
PREFERRED STOCKS AND SECURITIES (CONTINUED)
      FIXED RATE PREFERRED STOCKS AND SECURITIES (CONTINUED)
        FINANCIAL SERVICES (CONTINUED)
  174,950    Household Capital Trust II,
               8.70%..........................  $  4,603,372
             Lehman Brothers Holdings Inc.:
   19,900    8.30% QUICS, Series A............       503,719
  188,125    5.00% Conv. Pfd., Series B.......     5,667,266
   26,500    5.94% Pfd., Series C.............     1,185,875
   26,600    5.67% Pfd., Series D.............     1,137,150
             Merrill Lynch & Co., Inc.:
   30,000    8.00% TOPrS......................       815,625
  104,200    9.00% Pfd., Series A.............     3,288,812
                                                ------------
             TOTAL FINANCIAL SERVICES FIXED
               RATE PREFERRED STOCKS AND
               SECURITIES.....................    25,138,494
                                                ------------
        INSURANCE -- 8.2%
1,920,000    Allstate Financing II,
               7.83% 12/01/45 Capital
               Security.......................     2,073,600
  300,000    American General Capital A,
               7.57% 12/1/45 Capital Security
               144A**.........................       322,875
2,800,000    Aon Capital Trust A,
               8.205% 1/1/27 Capital
               Security.......................     3,220,000
   71,481    Hartford Capital II,
               8.35% QUIPS, Series B..........     1,880,844
3,700,000    MMI Capital Trust I,
               7.625% 12/15/27 Capital
               Security, Series B.............     3,700,000
2,950,000    Orion Capital Trust II,
               7.701% 4/15/28 Capital
               Security.......................     2,872,563
1,810,000    Provident Financing Trust I,
               7.405% 3/15/38 Capital
               Security.......................     1,814,525
       21    Prudential Human Resources
               Management Company, Inc.,
               6.30% Private Placement,
               Sinking Fund Pfd., Series A....     2,178,750
                                                ------------
             TOTAL INSURANCE FIXED RATE
               PREFERRED STOCKS AND
               SECURITIES.....................    18,063,157
                                                ------------
</TABLE>
 
<TABLE>
<CAPTION>
                                                   VALUE
SHARES/PAR                                        (NOTE 1)
- ----------                                        --------
<C>          <S>                                <C>
        MISCELLANEOUS INDUSTRIES -- 8.3%
    7,500    Anadarko Petroleum Corporation,
               5.46% Pfd. ....................  $    678,750
  118,300    Coastal Finance,
               8.375% TOPrS...................     2,947,149
   90,000    Cyprus AMAX Minerals Company,
               $4.00 Pfd., Series A...........     3,566,250
    3,000    Du Pont Nemours,
               $4.50 Pfd., Series B...........       270,750
   57,600    Farmland Industries Inc.,
               8.00% Pfd. 144A**..............     3,434,400
   30,000    LASMO America Ltd.,
               8.15% Pfd. 144A**..............     3,101,250
   30,000    Ocean Spray Cranberries,
               6.25% Pfd. 144A**..............     3,150,000
      475    Time Warner Inc.,
               10.25% Pfd., Series M..........       533,484
    9,520    Viad Corporation,
               $4.75 Sinking Fund Pfd. .......       725,900
                                                ------------
             TOTAL MISCELLANEOUS FIXED RATE
               PREFERRED STOCKS AND
               SECURITIES.....................    18,407,933
                                                ------------
             TOTAL FIXED RATE PREFERRED STOCKS
               AND SECURITIES.................   177,444,043
                                                ------------
             TOTAL PREFERRED STOCKS AND
               SECURITIES (Cost
               $194,909,264)..................   207,909,102
                                                ------------
COMMON STOCKS -- 1.4%
        UTILITIES -- 1.4%
   70,500    Nevada Power Company.............     1,669,969
   14,000    New England Electric System......       585,375
   14,800    Wisconsin Energy Corporation.....       457,875
    9,900    WPS Resources Corporation........       331,959
                                                ------------
             TOTAL UTILITY COMMON STOCKS
               (Cost $2,722,622)..............     3,045,178
                                                ------------
OPTION CONTRACTS -- 0.5% (Cost $2,105,737)
             March Put Options on U.S.
               Treasury Bond Futures, expiring
               2/20/99+.......................       975,781
                                                ------------
</TABLE>
 
                       See Notes to Financial Statements.

 
                                       11

<PAGE>
- --------------------------------------------------------------------------------
Preferred Income Opportunity Fund Incorporated
PORTFOLIO OF INVESTMENTS (CONTINUED)
NOVEMBER 30, 1998
- ---------------------------------------------------------------
 
<TABLE>
<CAPTION>
PRINCIPAL                                         VALUE
  AMOUNT                                         (NOTE 1)
- ---------                                        --------
<C>          <S>                               <C>
REPURCHASE AGREEMENT -- 2.8% (Cost $6,287,000)
$6,287,000   Agreement with UBS Securities
               Inc., 5.25% dated 11/30/98, to be
               repurchased at $6,287,917 on
               12/1/98, collateralized by
               $5,487,000 U.S. Treasury Note,
               6.50% due 11/15/26 (value
               $6,412,931)...................  $  6,287,000
                                               ------------
TOTAL INVESTMENTS (Cost $206,024,623*). 98.9%   218,217,061
OTHER ASSETS AND LIABILITIES (Net).....  1.1      2,472,561
                                       ------  ------------
NET ASSETS.............................100.0%  $220,689,622
                                       ======  ============
</TABLE>
 
- ---------------
 
 * Aggregate cost for Federal tax purposes is $204,782,466.
** Security exempt from registration under Rule 144A of the Securities Act of
   1933. These securities may be resold in transactions exempt from registration
   to qualified institutional buyers.
 + Non-income producing.
 
<TABLE>
ABBREVIATIONS (Note 6):
<S>    <C>
TOPrS  -- Trust Originated Preferred Securities
TIPS   -- Trust Issued Preferred Securities
QUIPS  -- Quarterly Income Preferred Securities
MIPS   -- Monthly Income Preferred Securities
QUIDS  -- Quarterly Income Debt Securities
QUICS  -- Quarterly Income Capital Securities
QIB    -- Quarterly Interest Bonds
</TABLE>
 
Capital Securities are debt instruments and the amounts shown in the Shares/Par
column are dollar amounts of par value.
 
                       See Notes to Financial Statements.



                                       12

<PAGE>
- --------------------------------------------------------------------------------
                                  Preferred Income Opportunity Fund Incorporated
                                             STATEMENT OF ASSETS AND LIABILITIES
                                                               NOVEMBER 30, 1998
                   -------------------------------------------------------------
 
<TABLE>
<S>                                                           <C>              <C>
ASSETS:
  Investments, at value (Cost $206,024,623) (Note 1) See
     accompanying schedule..................................                   $218,217,061
  Dividends and interest receivable.........................                      2,035,976
  Receivable for securities sold............................                      1,396,528
  Prepaid expenses..........................................                         25,986
                                                                               ------------
          Total Assets......................................                    221,675,551
LIABILITIES:
  Payable for securities purchased..........................  $   544,050
  Dividends payable to Common Shareholders..................      177,977
  Investment advisory fee payable (Note 2)..................      100,312
  Accrued expenses and other payables.......................      163,590
                                                              -----------
          Total Liabilities.................................                        985,929
                                                                               ------------
NET ASSETS..................................................                   $220,689,622
                                                                               ============
NET ASSETS consist of:
  Undistributed net investment income (Note 1)..............                   $  1,422,597
  Accumulated net realized gain on investments sold
     (Note 1)...............................................                      8,176,663
  Unrealized appreciation of investments (Note 3)...........                     12,192,438
  Par value of Common Stock.................................                        111,513
  Paid-in capital in excess of par value of Common Stock....                    128,786,411
  Money Market Cumulative Preferred(TM) Stock (Note 5)......                     70,000,000
                                                                               ------------
          Total Net Assets..................................                   $220,689,622
                                                                               ============
                                                               PER SHARE
                                                               --------- 
NET ASSETS AVAILABLE TO:
  Money Market Cumulative Preferred(TM) Stock (700 shares
     outstanding) redemption value..........................  $100,000.00      $ 70,000,000
  Accumulated undeclared dividends on Money Market
     Cumulative Preferred(TM) Stock.........................       225.36           157,753
                                                              -----------      ------------
                                                              $100,225.36        70,157,753
                                                              ===========
  Common Stock (11,151,287 shares outstanding)..............       $13.50       150,531,869
                                                                   ======      ------------

TOTAL NET ASSETS............................................                   $220,689,622
                                                                               ============
</TABLE>
 
                       See Notes to Financial Statements.


                                       13

<PAGE>
- --------------------------------------------------------------------------------
Preferred Income Opportunity Fund Incorporated
STATEMENT OF OPERATIONS
FOR THE YEAR ENDED NOVEMBER 30, 1998
- -----------------------------------------------
 
<TABLE>
<S>                                                           <C>             <C>
INVESTMENT INCOME:
     Dividends..............................................                  $11,870,040
     Interest...............................................                    3,051,862
                                                                              -----------
          Total Investment Income...........................                   14,921,902
EXPENSES:
     Investment advisory fee (Note 2).......................  $1,233,554
     Administration fee (Note 2)............................     268,296
     Money Market Cumulative Preferred(TM) broker
      commissions and Auction Agent fees....................     189,942
     Shareholder servicing agent fees (Note 2)..............      99,059
     Insurance expense......................................      77,922
     Legal and audit fees...................................      70,174
     Directors' fees and expenses (Note 2)..................      58,474
     Economic consulting fee (Note 2).......................      45,333
     Custodian fees (Note 2)................................      32,748
     Other..................................................     124,242
                                                              ----------
          Total Expenses....................................                    2,199,744
                                                                              -----------
NET INVESTMENT INCOME.......................................                   12,722,158
                                                                              -----------
REALIZED AND UNREALIZED GAIN ON INVESTMENTS
  (Notes 1 and 3):
     Net realized gain on investments sold during the
      year..................................................                    8,379,883
     Change in net unrealized appreciation/(depreciation)
      of investments during the year........................                   (6,412,102)
                                                                              -----------
NET REALIZED AND UNREALIZED GAIN ON INVESTMENTS.............                    1,967,781
                                                                              -----------
NET INCREASE IN NET ASSETS RESULTING FROM OPERATIONS........                  $14,689,939
                                                                              ===========
</TABLE>
 
                       See Notes to Financial Statements.


 
                                       14

<PAGE>
- --------------------------------------------------------------------------------
                                  Preferred Income Opportunity Fund Incorporated
                                              STATEMENT OF CHANGES IN NET ASSETS
                 ---------------------------------------------------------------
 
<TABLE>
<CAPTION>
                                                                 YEAR ENDED           YEAR ENDED
                                                              NOVEMBER 30, 1998    NOVEMBER 30, 1997
                                                              -----------------    -----------------
<S>                                                           <C>                  <C>
OPERATIONS:
     Net investment income..................................    $ 12,722,158         $ 12,304,022
     Net realized gain on investments sold during the
       year.................................................       8,379,883            2,977,646
     Change in net unrealized appreciation/(depreciation) of
       investments during the year..........................      (6,412,102)           6,639,359
                                                                ------------         ------------
     Net increase in net assets resulting from operations...      14,689,939           21,921,027
DISTRIBUTIONS:
     Dividends paid from net investment income to Money
       Market Cumulative Preferred(TM) Stock Shareholders
       (Note 5).............................................      (2,066,476)          (2,350,442)
     Distributions paid from net realized capital gains to
       Money Market Cumulative Preferred(TM) Stock
       Shareholders (Note 5)................................      (1,198,981)            (457,916)
     Dividends paid from net investment income to Common
       Stock Shareholders...................................      (9,921,815)         (10,345,646)
     Distributions paid from net realized capital gains to
       Common Stock Shareholders............................      (2,043,516)          (1,731,258)
                                                                ------------         ------------
NET INCREASE/(DECREASE) IN NET ASSETS FOR THE YEAR..........        (540,849)           7,035,765
NET ASSETS:
     Beginning of year......................................     221,230,471          214,194,706
                                                                ------------         ------------
     End of year (including undistributed net investment
       income of $1,422,597 and $623,523, respectively).....    $220,689,622         $221,230,471
                                                                ============         ============
</TABLE>
 
                       See Notes to Financial Statements.


 
                                       15

<PAGE>
- --------------------------------------------------------------------------------
Preferred Income Opportunity Fund Incorporated
FINANCIAL HIGHLIGHTS
FOR A COMMON SHARE OUTSTANDING THROUGHOUT EACH YEAR.
- -------------------------------------------------------------------
 
     Contained below is per share operating performance data, total investment
returns, ratios to average net assets and other supplemental data. This
information has been derived from information provided in the financial
statements and market price data for the Fund's shares.
 
<TABLE>
<CAPTION>
                                                                               YEAR ENDED NOVEMBER 30,
                                                              ---------------------------------------------------------
                                                                1998        1997        1996        1995        1994
                                                              --------    --------    --------    --------    ---------
<S>                                                           <C>         <C>         <C>         <C>         <C>
OPERATING PERFORMANCE:
Net asset value, beginning of year..........................  $  13.53    $  12.91    $  12.35    $  10.92    $   13.17
                                                              --------    --------    --------    --------    ---------
Net investment income.......................................      1.14        1.10        1.16        1.27         1.19
Net realized and unrealized gain/(loss) on investments......      0.17        0.87        0.53        1.73        (1.64)
                                                              --------    --------    --------    --------    ---------
Total from investment operations............................      1.31        1.97        1.69        3.00        (0.45)
                                                              --------    --------    --------    --------    ---------
DISTRIBUTIONS:
Dividends paid from net investment income to MMP*
 Shareholders...............................................     (0.18)      (0.21)      (0.21)      (0.31)       (0.18)
Distributions paid from net realized capital gains to MMP*
 Shareholders...............................................     (0.11)      (0.04)      (0.03)      (0.00)#      (0.03)
Dividends paid from net investment income to Common Stock
 Shareholders...............................................     (0.89)      (0.92)      (0.87)      (1.11)       (0.86)
Distributions paid from net realized capital gains to Common
 Stock Shareholders.........................................     (0.18)      (0.16)         --       (0.17)       (0.72)
Change in accumulated undeclared dividends on MMP*..........      0.02       (0.02)      (0.02)       0.02        (0.01)
                                                              --------    --------    --------    --------    ---------
Total Distributions.........................................     (1.34)      (1.35)      (1.13)      (1.57)       (1.80)
                                                              --------    --------    --------    --------    ---------
Net asset value, end of year................................  $  13.50    $  13.53    $  12.91    $  12.35    $   10.92
                                                              ========    ========    ========    ========    =========
Market value, end of year...................................  $ 12.875    $ 12.875    $ 12.000    $ 11.250    $  10.125
                                                              ========    ========    ========    ========    =========
Total Investment return based on net asset value**..........     8.29%      14.44%      13.11%      27.25%      (5.44)%
                                                              ========    ========    ========    ========    =========
Total Investment return based on market value**.............     8.53%      17.16%      15.42%      25.02%     (12.83)%
                                                              ========    ========    ========    ========    =========
RATIOS TO AVERAGE NET ASSETS AVAILABLE TO COMMON STOCK
 SHAREHOLDERS:
   Operating expenses.......................................      1.45%       1.48%       1.71%       1.78%        1.69%
   Net investment income***.................................      6.37%       6.44%       7.36%       8.47%        8.31%
SUPPLEMENTAL DATA:
   Portfolio turnover rate..................................        87%         74%         87%         94%         116%
   Net assets, end of year (in 000's).......................  $220,690    $221,230    $214,195    $207,720     $191,797
============================================================
Ratio of operating expenses to Total Average Net Assets
 including MMP*.............................................      0.99%       1.00%       1.13%       1.13%        1.11%
</TABLE>


  * Money Market Cumulative Preferred(TM) Stock.
 ** Assumes reinvestment of distributions at the price obtained by the Fund's
    Dividend Reinvestment Plan.
*** The net investment income ratios reflect income net of operating expenses
    and payments to MMP* Shareholders.
 #  Amount represents less than $0.01 per share.
 
                       See Notes to Financial Statements.
 
                                       16

<PAGE>
- --------------------------------------------------------------------------------
                                  Preferred Income Opportunity Fund Incorporated
                                                FINANCIAL HIGHLIGHTS (CONTINUED)
                          ------------------------------------------------------
 
     The table below sets out information with respect to Money Market
Cumulative Preferred(TM) Stock currently outstanding.
 
<TABLE>
<CAPTION>
                                      INVOLUNTARY         AVERAGE
                            ASSET     LIQUIDATING          MARKET
           TOTAL SHARES   COVERAGE     PREFERENCE          VALUE
           OUTSTANDING    PER SHARE   PER SHARE(1)   PER SHARE(1) & (2)
           ------------   ---------   ------------   ------------------
<S>        <C>            <C>         <C>            <C>
11/30/98       700        $315,271      $100,000          $100,000
11/30/97       700         316,044       100,000           100,000
11/30/96       700         305,992       100,000           100,000
11/30/95       700         296,743       100,000           100,000
11/30/94       700         273,996       100,000           100,000
</TABLE>
 
- ---------------
(1) Excludes accumulated undeclared dividends.
(2) See Note 5.







 
                       See Notes to Financial Statements.


 
                                       17

<PAGE>
- --------------------------------------------------------------------------------
Preferred Income Opportunity Fund Incorporated
NOTES TO FINANCIAL STATEMENTS
- -----------------------------------------------------

 
1.   SIGNIFICANT ACCOUNTING POLICIES
 
     Preferred Income Opportunity Fund Incorporated (the "Fund") is a
diversified, closed-end management investment company organized as a Maryland
corporation and is registered with the Securities and Exchange Commission
("SEC") under the Investment Company Act of 1940, as amended. The policies
described below are followed consistently by the Fund in the preparation of its
financial statements in conformity with generally accepted accounting
principles.
 
     Portfolio valuation:  The net asset value of the Fund's Common Stock is
determined by the Fund's administrator no less frequently than on the last
business day of each week and month. It is determined by dividing the value of
the Fund's net assets attributable to common shares by the number of shares of
Common Stock outstanding. The value of the Fund's net assets attributable to
common shares is deemed to equal the value of the Fund's total assets less (i)
the Fund's liabilities, (ii) the aggregate liquidation value of the outstanding
Money Market Cumulative Preferred(TM) Stock and (iii) accumulated and unpaid
dividends on the outstanding Money Market Cumulative Preferred(TM) Stock.
Securities listed on a national securities exchange are valued on the basis of
the last sale on such exchange on the day of valuation. In the absence of sales
of listed securities and with respect to securities for which the most recent
sale prices are not deemed to represent fair market value and unlisted
securities (other than money market instruments), securities are valued at the
mean between the closing bid and asked prices when quoted prices for investments
are readily available. Investments for which market quotations are not readily
available are valued at fair value as determined in good faith by or under the
direction of the Board of Directors of the Fund, including reference to
valuations of other securities which are considered comparable in quality,
maturity and type. Investments in money market instruments, which mature in 60
days or less, are valued at amortized cost.
 
     Securities transactions and investment income:  Securities transactions are
recorded as of the trade date. Realized gains and losses from securities sold
are recorded on the identified cost basis. Dividend income is recorded on
ex-dividend dates. Interest income is recorded on the accrual basis.
 
     Option accounting principles:  Upon the purchase of a put option by the
Fund, the total purchase price paid is recorded as an investment. The market
valuation is determined as set forth in the second preceding paragraph. When the
Fund enters into a closing sale transaction, the Fund will record a gain or loss
depending on the difference between the purchase and sale price. The risks
associated with purchasing options and the maximum loss the Fund would incur are
limited to the purchase price originally paid.
 
     Repurchase Agreements:  The Fund may engage in repurchase agreement
transactions. The Fund's Board of Directors reviews and approves periodically
the eligibility of the banks and dealers with which the Fund enters into
repurchase agreement transactions. The value of the collateral underlying such
transactions is at least equal at all times to the total amount of the
repurchase obligations, including interest. The Fund maintains possession of the
collateral and, in the event of counterparty default, the Fund has the right to
use the collateral to offset losses incurred. There is the possibility of loss
to the




                                       18

<PAGE>
- --------------------------------------------------------------------------------
                                  Preferred Income Opportunity Fund Incorporated
                                       NOTES TO FINANCIAL STATEMENTS (CONTINUED)
        ------------------------------------------------------------------------
 
Fund in the event the Fund is delayed or prevented from exercising its rights to
dispose of the collateral securities.
 
     Dividends and distributions to shareholders:  The Fund expects to declare
dividends on a monthly basis to shareholders of Common Stock. The shareholders
of Money Market Cumulative Preferred(TM) Stock are entitled to receive
cumulative cash dividends as declared by the Fund's Board of Directors.
Distributions to shareholders are recorded on the ex-dividend date. Any net
realized short-term capital gains will be distributed to shareholders at least
annually. Any net realized long-term capital gains may be distributed to
shareholders at least annually or may be retained by the Fund as determined by
the Fund's Board of Directors. Capital gains retained by the Fund are subject to
tax at the corporate tax rate. Subject to the Fund qualifying as a regulated
investment company, any taxes paid by the Fund on such net realized long-term
gains may be used by the Fund's Shareholders as a credit against their own tax
liabilities.
 
     Federal income taxes:  The Fund intends to continue to qualify as a
regulated investment company by complying with the requirements under subchapter
M of the Internal Revenue Code of 1986, as amended, applicable to regulated
investment companies and intends to distribute substantially all of its taxable
net investment income to its shareholders. Therefore, no Federal income tax
provision is required.
 
     Income and capital gain distributions are determined and characterized in
accordance with income tax regulations which may differ from generally accepted
accounting principles. These differences are primarily due to (1) differing
treatments of income and gains on various investment securities held by the
Fund, including timing differences, (2) the attribution of expenses against
certain components of taxable investment income, and (3) federal regulations
requiring proportional allocation of income and gains to all classes of
Shareholders.
 
     The Internal Revenue Code of 1986, as amended, imposes a 4% nondeductible
excise tax on the Fund to the extent the Fund does not distribute by the end of
any calendar year at least (1) 98% of the sum of its net investment income for
that year and its capital gains (both long term and short term) for its fiscal
year and (2) certain undistributed amounts from previous years.
 
     Other:  The preparation of financial statements in accordance with
generally accepted accounting principles requires management to make estimates
and assumptions that affect the reported amounts and disclosures in the
financial statements. Actual results could differ from those estimates.
 
2.   INVESTMENT ADVISORY FEE, DIRECTORS' FEES, ECONOMIC CONSULTING FEE,
     ADMINISTRATION FEE AND TRANSFER AGENT FEE
 
     Flaherty & Crumrine Incorporated (the "Adviser") serves as the Fund's
Investment Adviser. The Fund pays the Adviser a monthly fee at an annual rate of
0.625% of the value of the Fund's average monthly net assets up to $100 million
and 0.50% of the value of the Fund's average monthly net assets in excess of
$100 million.



                                       19

<PAGE>
- --------------------------------------------------------------------------------
Preferred Income Opportunity Fund Incorporated
NOTES TO FINANCIAL STATEMENTS (CONTINUED)
- ------------------------------------------------------------------------
 
     The Fund currently pays each Director who is not a director, officer or
employee of the Adviser a fee of $9,000 per annum, plus $500 for each in-person
meeting of the Board of Directors or any committee and $100 for each telephone
meeting. In addition, the Fund will reimburse all Directors for travel and out-
of-pocket expenses incurred in connection with such meetings.
 
     Primark Decision Economics Inc. ("Primark") serves as the Fund's Economic
Consultant. The Fund pays Primark an annual fee equal to $45,333 for services
provided.
 
     First Data Investor Services Group, Inc. ("Investor Services Group"), a
wholly owned subsidiary of First Data Corporation, serves as the Fund's
Administrator and Transfer Agent. As Administrator, Investor Services Group
calculates the net asset value of the Fund's shares and generally assists in all
aspects of the Fund's administration and operation. As compensation for Investor
Services Group's services as Administrator, the Fund pays Investor Services
Group a monthly fee at an annual rate of 0.12% of the Fund's average monthly net
assets. Boston Safe Deposit and Trust Company ("Boston Safe"), a wholly owned
subsidiary of Mellon Bank Corporation, serves as the Fund's Custodian. As
compensation for Boston Safe's services as Custodian, the Fund pays Boston Safe
a monthly fee at an annual rate of 0.01% of the Fund's average monthly net
assets. Investor Services Group also serves as the Fund's Common Stock servicing
agent (transfer agent), dividend-paying agent and registrar, and as compensation
for Investor Services Group's services as transfer agent, the Fund pays Investor
Services Group a fee at an annual rate of 0.02% of the Fund's average monthly
net assets plus certain out-of-pocket expenses.
 
     Chase Manhattan Bank ("Auction Agent") serves as the Fund's Money Market
Cumulative Preferred(TM) Stock transfer agent, registrar, dividend disbursing
agent and redemption agent.
 
3.   PURCHASES AND SALES OF SECURITIES
 
     Cost of purchases and proceeds from sales of securities for the year ended
November 30, 1998, excluding short-term investments, aggregated $188,896,861 and
$202,996,639, respectively.
 
     At November 30, 1998, aggregate gross unrealized appreciation for all
securities in which there is an excess of value over tax cost was $14,315,934
and aggregate gross unrealized depreciation for all securities in which there is
an excess of tax cost over value was $881,339.
 
4.   COMMON STOCK
 
     At November 30, 1998, 240,000,000 shares of $0.01 par value Common Stock
were authorized. There were no Common Stock transactions for the years ended
November 30, 1998 and 1997.
 
5.   MONEY MARKET CUMULATIVE PREFERRED(TM) STOCK
 
     The Fund's Articles of Incorporation authorize the issuance of up to
10,000,000 shares of $0.01 par value preferred stock. The Money Market
Cumulative Preferred(TM) Stock is senior to the Common Stock



                                       20

<PAGE>
- --------------------------------------------------------------------------------
                                  Preferred Income Opportunity Fund Incorporated
                                       NOTES TO FINANCIAL STATEMENTS (CONTINUED)
        ------------------------------------------------------------------------
 
and results in the financial leveraging of the Common Stock. Such leveraging
tends to magnify both the risks and opportunities to Common Stock Shareholders.
Dividends on shares of Money Market Cumulative Preferred(TM) Stock are
cumulative.
 
     The Fund is required to meet certain asset coverage tests with respect to
the Money Market Cumulative Preferred(TM) Stock. If the Fund fails to meet these
requirements and does not correct such failure, the Fund may be required to
redeem, in part or in full, Money Market Cumulative Preferred(TM) Stock at a
redemption price of $100,000 per share plus an amount equal to the accumulated
and unpaid dividends on such shares in order to meet these requirements.
Additionally, failure to meet the foregoing asset requirements could restrict
the Fund's ability to pay dividends to Common Stock Shareholders and could lead
to sales of portfolio securities at inopportune times.
 
     If the Fund allocates any net gains or income ineligible for the Dividends
Received Deduction to shares of the Money Market Cumulative Preferred(TM) Stock,
the Fund is required to make additional distributions to Money Market Cumulative
Preferred(TM) Stock Shareholders or to pay a higher dividend rate in amounts
needed to provide a return, net of tax, equal to the return had such originally
paid distributions been eligible for the Dividends Received Deduction.
 
     An auction of the Money Market Cumulative Preferred(TM) Stock is generally
held every 49 days. Existing shareholders may submit an order to hold, bid or
sell such shares at par value on each auction date. Money Market Cumulative
Preferred(TM) Stock Shareholders may also trade shares in the secondary market
between auction dates.
 
     At November 30, 1998, 700 shares of Money Market Cumulative Preferred(TM)
Stock were outstanding at the annual rate of 4.270%. The dividend rate, as set
by the auction process, is generally expected to vary with short-term interest
rates. These rates may vary in a manner unrelated to the income received on the
Fund's assets, which could have either a beneficial or detrimental impact on net
investment income and gains available to Common Stock Shareholders. While the
Fund expects to structure the portfolio holdings and hedging transactions to
lessen such risks to Common Stock Shareholders, there can be no assurance that
such results will be attained.
 
6.   PORTFOLIO INVESTMENTS, CONCENTRATION AND INVESTMENT QUALITY
 
     The Fund invests primarily in adjustable and fixed rate preferred stocks
and similar hybrid securities. Under normal market conditions, the Fund invests
at least 25% of its assets in securities issued by utilities and may invest a
significant portion of its assets, but less than 25% of its assets, in companies
in the banking industry. The Fund's portfolio may therefore be subject to
greater risk and market fluctuation than a portfolio of securities representing
a broader range of investment alternatives. Because of the Fund's concentration
of investments in the utility industry and significant holdings in the banking
industry, the ability of the Fund to maintain its dividend and the value of the
Fund's investments could be adversely affected by the possible inability of
companies in these industries to pay dividends and interest on their securities
and the ability of holders of securities of such companies to realize any value
from the assets of




                                       21

<PAGE>
- --------------------------------------------------------------------------------
Preferred Income Opportunity Fund Incorporated
NOTES TO FINANCIAL STATEMENTS (CONTINUED)
- ------------------------------------------------------------------------
 
the issuer upon liquidation or bankruptcy. The Fund may invest up to 15% of its
assets at the time of purchase in securities rated below investment grade,
provided that no such investment may be rated below both "Ba" by Moody's
Investors Service, Inc. and "BB" by Standard & Poor's Rating Group or judged to
be comparable in quality at the time of purchase; however, any such securities
must be issued by an issuer having an outstanding class of senior debt rated
investment grade. The Fund may also invest up to 15% of its assets in common
stock. Under normal conditions, the Fund may invest up to 35% of its assets in
debt securities. Certain of its investments in hybrid or taxable preferred
securities, such as TOPrS, TIPS, QUIPS, MIPS, QUIDS, QUICS, QIB's, Capital
Securities, and other similar or related investments, will be subject to the
foregoing 35% limitation to the extent that, in the opinion of the Fund's
Adviser, such investments are deemed to be debt-like in key characteristics.
 
7.   SPECIAL INVESTMENT TECHNIQUES
 
     The Fund may employ certain investment techniques in accordance with its
fundamental investment policies. These may include the use of when-issued and
delayed delivery transactions. Securities purchased or sold on a when-issued or
delayed delivery basis may be settled within 45 days after the date of the
transaction. Such transactions may expose the Fund to credit and market
valuation risk greater than that associated with regular trade settlement
procedures. The Fund may also enter into transactions, in accordance with its
fundamental investment policies, involving any or all of the following: lending
of portfolio securities, short sales of securities, futures contracts, options
on futures contracts, and options on securities. With the exception of
purchasing securities on a when-issued or delayed delivery basis or lending
portfolio securities, these transactions are used for hedging or other
appropriate risk-management purposes or, under certain other circumstances, to
increase income. As of November 30, 1998, the Fund owned put options on U.S.
Treasury bond futures contracts. No assurance can be given that such
transactions will achieve their desired purposes or will result in an overall
reduction of risk to the Fund.
 
8.   SIGNIFICANT SHAREHOLDERS
 
     At November 30, 1998, the Commerce Group, Inc. owned approximately 25% of
the total Common Stock Fund shares.
 
9.   SUBSEQUENT EVENTS
 
     On December 14, 1998, the Fund declared a distribution of $0.81 per share
(of which for tax purposes $0.3346 per share represents a dividend from ordinary
income and $0.4754 per share represents a dividend from realized long term
capital gains) to Common Stock Shareholders of record December 24, 1998, payable
December 31, 1998.
 
     As a result of the gains realized by the Fund, a portion of the
distributions paid to the Fund's Money Market Cumulative Preferred(TM) Stock
Shareholders from January 1, 1998 through November 30, 1998 has been designated
as being from long term capital gains, as required by ruling 89-81 of the
Internal Revenue Code of 1986, as amended. On December 21, 1998, the Fund
declared an additional distribution of $575,316 payable December 23, 1998 to
Money Market Cumulative Preferred(TM) Stock Shareholders as required by the
Fund's Articles Supplementary. This additional distribution is required to
reflect the fact that the original distributions did not qualify 100% for the
Corporate Dividends Received Deduction.




                                       22

<PAGE>
                       REPORT OF INDEPENDENT ACCOUNTANTS
 
To the Shareholders and Board of Directors of
  Preferred Income Opportunity Fund Incorporated:
 
     In our opinion, the accompanying statement of assets and liabilities,
including the portfolio of investments, 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 Preferred Income Opportunity Fund
Incorporated (the "Fund") at November 30, 1998, 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 November 30, 1998 by correspondence with the
custodian and brokers, provide a reasonable basis for the opinion expressed
above.
 
Boston, Massachusetts                                 PricewaterhouseCoopers LLP
January 15, 1999



 
                                       23

<PAGE>
- --------------------------------------------------------------------------------
Preferred Income Opportunity Fund Incorporated
TAX INFORMATION (UNAUDITED)
- ----------------------------------------------
 
     For the fiscal year ended November 30, 1998, the Fund realized and, by
December 31, 1998, had distributed long term capital gains to both Common Stock
Shareholders and Money Market Cumulative Preferred(TM) Stock Shareholders of
$6,463,321. The amount may differ from those shown elsewhere in this annual
report due to differences in the calculation of long term gains for tax purposes
as compared with SEC financial reporting requirements. Of the total
distributions attributable to the fiscal year ended November 30, 1998, including
the Additional Distribution to Money Market Cumulative Preferred(TM) Stock
Shareholders, 42.73% qualified for the Dividends Received Deduction for eligible
corporate investors. (See Note 9).
 
     For the calendar year ended December 31, 1998, 42.76% of all distributions
paid to Common Stock Shareholders qualified for the Dividends Received Deduction
for eligible corporate investors. Shareholders should refer to Form 1099
accompanying additional information and the information contained herein when
preparing their tax returns to determine the appropriate tax characterization of
the distributions they received from the Fund in calendar year 1998.
 
- --------------------------------------------------------------------------------
                                  Preferred Income Opportunity Fund Incorporated
                           QUARTERLY RESULTS OF INVESTMENT OPERATION (UNAUDITED)
- --------------------------------------------------------------------------------
 
<TABLE>
<CAPTION>
                                               AVAILABLE TO COMMON STOCK SHAREHOLDERS
                                 ------------------------------------------------------------------
                                                             NET REALIZED
                                                            AND UNREALIZED         NET INCREASE
                                                             GAIN/(LOSS)        IN NET ASSETS FROM
            INVESTMENT INCOME    NET INVESTMENT INCOME      ON INVESTMENTS          OPERATIONS
           -------------------   ---------------------   --------------------   -------------------
QUARTER                  PER                     PER                    PER                   PER
 ENDED       TOTAL      SHARE*      TOTAL       SHARE*      TOTAL      SHARE*     TOTAL      SHARE*
- -------      -----      ------      -----       ------      -----      ------     -----      ------
<S>        <C>          <C>      <C>            <C>      <C>           <C>      <C>          <C>
02/28/97   $3,328,538   $0.30    $2,789,856     $0.25    $  (233,256)  $(0.02)  $2,556,600   $0.23
05/31/97    3,714,170    0.33     3,218,380      0.29      2,151,212     0.19    5,369,592    0.48
08/31/97    3,747,750    0.34     3,195,496      0.29      4,544,355     0.41    7,739,851    0.70
11/30/97    3,653,782    0.33     3,100,290      0.27      3,154,694     0.29    6,254,984    0.56
02/28/98    3,784,203    0.33     3,233,347      0.29      2,711,296     0.24    5,944,643    0.53
05/31/98    3,593,404    0.32     3,028,370      0.27      1,971,753     0.17    5,000,123    0.44
08/31/98    3,730,062    0.33     3,160,444      0.28       (894,789)   (0.08)   2,265,655    0.20
11/30/98    3,814,233    0.34     3,299,997      0.30     (1,820,479)   (0.16)   1,479,518    0.14
</TABLE>
 
- ---------------
* Per share of common stock.



 
                                       24

<PAGE>
- --------------------------------------------------------------------------------
                                  Preferred Income Opportunity Fund Incorporated
                                              ADDITIONAL INFORMATION (UNAUDITED)
                     -----------------------------------------------------------
 
DIVIDEND REINVESTMENT AND CASH PURCHASE PLAN
 
     Under the Fund's Dividend Reinvestment and Cash Purchase Plan (the "Plan"),
a shareholder whose Common Stock is registered in his own name will have all
distributions reinvested automatically by Investor Services Group as agent under
the Plan, unless the shareholder elects to receive cash. Distributions with
respect to shares registered in the name of a broker-dealer or other nominee
(that is, in "street name") may be reinvested by the broker or nominee in
additional shares under the Plan, but only if the service is provided by the
broker or nominee, unless the shareholder elects to receive distributions in
cash. A shareholder who holds Common Stock registered in the name of a broker or
other nominee may not be able to transfer the Common Stock to another broker or
nominee and continue to participate in the Plan. Investors who own Common Stock
registered in street name should consult their broker or nominee for details
regarding reinvestment.
 
     The number of shares of Common Stock distributed to participants in the
Plan in lieu of a cash dividend is determined in the following manner. Whenever
the market price per share of the Fund's Common Stock is equal to or exceeds the
net asset value per share on the valuation date, participants in the Plan will
be issued new shares valued at the higher of net asset value or 95% of the then
current market value. Otherwise, Investor Services Group will buy shares of the
Fund's Common Stock in the open market, on the New York Stock Exchange or
elsewhere, on or shortly after the payment date of the dividend or distribution
and continuing until the ex-dividend date of the Fund's next distribution to
holders of the Common Stock or until it has expended for such purchases all of
the cash that would otherwise be payable to the participants. The number of
purchased shares that will then be credited to the participants' accounts will
be based on the average per share purchase price of the shares so purchased,
including brokerage commissions. If Investor Services Group commences purchases
in the open market and the then current market price of the shares (plus any
estimated brokerage commissions) subsequently exceeds their net asset value most
recently determined before the completion of the purchases, Investor Services
Group will attempt to terminate purchases in the open market and cause the Fund
to issue the remaining dividend or distribution in shares. In this case, the
number of shares received by the participant will be based on the weighted
average of prices paid for shares purchased in the open market and the price at
which the Fund issues the remaining shares. These remaining shares will be
issued by the Fund at the higher of net asset value or 95% of the then current
market value.
 
     Plan participants are not subject to any charge for reinvesting dividends
or capital gains distributions. Each Plan participant will, however, bear a
proportionate share of brokerage commissions incurred with respect to Investor
Services Group's open market purchases in connection with the reinvestment of
dividends or capital gains distributions. For the year ended November 30, 1998,
$7,125 in brokerage commissions were incurred.
 
     The automatic reinvestment of dividends and capital gains distributions
will not relieve Plan participants of any income tax that may be payable on the
dividends or capital gains distributions. A participant in the Plan will be
treated for Federal income tax purposes as having received, on the dividend



 
                                       25

<PAGE>
- --------------------------------------------------------------------------------
Preferred Income Opportunity Fund Incorporated
ADDITIONAL INFORMATION (UNAUDITED) (CONTINUED)
- ------------------------------------------------------------------------------
 
payment date, a dividend or distribution in an amount equal to the cash that the
participant could have received instead of shares.
 
     In addition to acquiring shares of Common Stock through the reinvestment of
cash dividends and distributions, a shareholder may invest any further amounts
from $100 to $3,000 semi-annually at the then current market price in shares
purchased through the Plan. Such semi-annual investments are subject to any
brokerage commission charges incurred.
 
     A shareholder whose Common Stock is registered in his or her own name may
terminate participation in the Plan at any time by notifying Investor Services
Group in writing, by completing the form on the back of the Plan account
statement and forwarding it to Investor Services Group or by calling Investor
Services Group directly. A termination will be effective immediately if notice
is received by Investor Services Group not less than 10 days before any dividend
or distribution record date. Otherwise, the termination will be effective, and
only with respect to any subsequent dividends or distributions, on the first day
after the dividend or distribution has been credited to the participant's
account in additional shares of the Fund. Upon termination and according to a
participant's instructions, Investor Services Group will either (a) issue
certificates for the whole shares credited to the shareholder's Plan account and
a check representing any fractional shares or (b) sell the shares in the market.
Shareholders who hold common stock registered in the name of a broker or other
nominee should consult their broker or nominee to terminate participation.
 
     The Plan is described in more detail in the Fund's Plan brochure.
Information concerning the Plan may be obtained from Investor Services Group at
1-800-331-1710.


 
                                       26

<PAGE>
DIRECTORS
  Martin Brody
  Donald F. Crumrine, CFA                                             PREFERRED
  Robert T. Flaherty, CFA                                              INCOME
  David Gale                                                         OPPORTUNITY
  Morgan Gust                                                        -----------
  Robert F. Wulf, CFA                                                    FUND
                                                                     -----------
OFFICERS
  Robert T. Flaherty, CFA
    Chairman of the Board
    and President
  Donald F. Crumrine, CFA
    Vice President
    and Secretary
  Robert M. Ettinger, CFA
    Vice President
  Peter C. Stimes, CFA
    Vice President
    and Treasurer
  Carl D. Johns
    Assistant Treasurer

INVESTMENT ADVISER                                                       Annual
  Flaherty & Crumrine Incorporated                                       Report
  e-mail: [email protected]
 
QUESTIONS CONCERNING YOUR SHARES OF PREFERRED
  INCOME OPPORTUNITY FUND?

  - If your shares are held in a Brokerage
    Account, contact your Broker.

  - If you have physical possession of your
    shares in certificate form, contact the
    Fund's Transfer Agent & Shareholder
    Servicing Agent --
       First Data Investor Services Group, Inc.
           P.O. Box 1376
           Boston, MA 02104
           1-800-331-1710
 
THIS REPORT IS SENT TO SHAREHOLDERS OF
PREFERRED INCOME OPPORTUNITY FUND
INCORPORATED FOR THEIR INFORMATION. IT IS NOT
A PROSPECTUS, CIRCULAR OR REPRESENTATION
INTENDED FOR USE IN THE PURCHASE OR SALE OF
SHARES OF THE FUND OR OF ANY SECURITIES
MENTIONED IN THIS REPORT.                                      November 30, 1998
 



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