ROSLYN BANCORP INC, DEF 14A, 2000-04-17

ROSLYN BANCORP INC
DEF 14A, 2000-04-17
SAVINGS INSTITUTIONS, NOT FEDERALLY CHARTERED

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SCHEDULE 14-A INFORMATION

Proxy Statement Pursuant to Section 14(a) of the Securities
Exchange Act of 1934 (Amendment No. _)

Filed by the Registrant [X]

Filed by a Party other than the Registrant [_]

Check the appropriate box:

[_] Preliminary Proxy Statement

[_] Confidential, For Use of the Commission Only (as permitted by Rule
14a-6(e)(2))

[X] Definitive Proxy Statement

[_] Definitive Additional Materials

[_] Soliciting Material Pursuant to (S)240.14a-11(c) or (S)240.14a-12

ROSLYN BANCORP, INC.
- --------------------------------------------------------------------------------
(Name of Registrant as Specified In Its Charter)

- --------------------------------------------------------------------------------
(Name of Person(s) Filing Proxy Statement, if other than Registrant)

Payment of Filing Fee (Check the appropriate box):

[X] No fee required.

[_] Fee computed on table below per Exchange Act Rules 14a-6(i)(1) and 0-11

(1) Title of each class of securities to which transaction applies:

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(2) Aggregate number of securities to which transaction applies:

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(3) Per unit price or other underlying value of transaction computed
pursuant to Exchange Act Rule 0-11 (set forth the amount on which
the filing fee is calculated and state how it was determined):

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(4) Proposed maximum aggregate value of transaction:

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(5) Total fee paid:

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[_] Fee paid previously with preliminary materials.

[_] Check box if any part of the fee is offset as provided by Exchange
Act Rule 0-11(a)(2) and identify the filing for which the offsetting fee
was paid previously. Identify the previous filing by registration statement
number, or the Form or Schedule and the date of its filing.

(1) Amount Previously Paid:

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(2) Form, Schedule or Registration Statement No.:

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(3) Filing Party:

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(4) Date Filed:

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[ROSLYN LOGO APPEARS HERE]
1400 Old Northern Boulevard
Roslyn, New York 11576
(516) 621-6000

April 17, 2000

Fellow Stockholders:

You are cordially invited to attend the Annual Meeting of Stockholders of
Roslyn Bancorp, Inc. (the "Company"), the holding company for The Roslyn Savings
Bank (the "Bank"). The Annual Meeting will be held on Wednesday, May 24, 2000,
at 9:30 a.m., Eastern time, at the Milleridge Cottage, 585 North Broadway,
Jericho, New York.

The attached Notice of Annual Meeting and the Proxy Statement describe the
formal business to be transacted at the Annual Meeting. Directors and officers
of the Company, as well as a representative of KPMG LLP, the Company's
independent auditors, will be present at the Annual Meeting to respond to any
questions that our stockholders may have regarding the business to be
transacted.

The Board of Directors of Roslyn Bancorp, Inc. has determined that the
matters to be considered at the Annual Meeting are in the best interests of the
Company and its stockholders. For the reasons set forth in the Proxy Statement,
the Board unanimously recommends that you vote "FOR" each matter to be
considered.

Last year, over 88% of the outstanding shares were represented at the
annual meeting. It is important that your shares are represented this year
whether or not you are personally able to attend the Annual Meeting. This year,
registered stockholders can vote their shares via the Internet or by using a
toll-free telephone number. Instructions for using these convenient new
services are provided on the proxy card. Of course, you may still vote your
shares by proxy by signing and returning the enclosed proxy card promptly. Your
cooperation is appreciated since a majority of the Company's common stock must
be represented, either in person or by proxy, to constitute a quorum for the
conduct of business.

On behalf of the Board of Directors and all of the employees of the Company
and the Bank, we thank you for your continued interest and support.

Sincerely yours,

/s/ Joseph L. Mancino /s/ John M. Tsimbinos
Joseph L. Mancino John M. Tsimbinos
President, Chief Executive Officer and Chairman of the Board
Vice Chairman of the Board
<PAGE>

ROSLYN BANCORP, INC.
1400 OLD NORTHERN BOULEVARD
ROSLYN, NEW YORK 11576

__________________________________

NOTICE OF ANNUAL MEETING OF STOCKHOLDERS
To Be Held on May 24, 2000

NOTICE IS HEREBY GIVEN that the Annual Meeting of Stockholders (the "Annual
Meeting") of Roslyn Bancorp, Inc. (the "Company") will be held on Wednesday, May
24, 2000, at 9:30 a.m., Eastern time, at the Milleridge Cottage, 585 North
Broadway, Jericho, New York.

The purpose of the Annual Meeting is to consider and vote upon the
following matters:

1. the election of five Directors to three-year terms of office each;

2. the ratification of the appointment of KPMG LLP as independent auditors
of the Company for the fiscal year ending December 31, 2000; and

3. such other matters as may properly come before the Annual Meeting and at
any adjournment of the Annual Meeting, including whether or not to
adjourn the Annual Meeting.

The Board of Directors has established March 29, 2000 as the record date
for the determination of stockholders entitled to receive notice of and to vote
at the Annual Meeting and at any adjournment of the Annual Meeting. Only record
holders of the Company's common stock as of the close of business on March 29,
2000 will be entitled to vote at the Annual Meeting, or at any adjournments of
the Annual Meeting. If there are not enough votes to constitute a quorum, or to
approve or ratify any of the foregoing proposals at the time of the Annual
Meeting, the Annual Meeting may be adjourned in order to permit further
solicitation of proxies by the Company. A list of stockholders entitled to vote
at the Annual Meeting will be available for inspection at Roslyn Bancorp, Inc.,
1400 Old Northern Boulevard, Roslyn, New York, for a period of 10 days before
the Annual Meeting and will also be available for inspection at the Annual
Meeting.

By Order of the Board of Directors

/s/ R. Patrick Quinn
R. Patrick Quinn
Corporate Secretary

Roslyn, New York
April 17, 2000
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YOUR VOTE IS IMPORTANT
REGARDLESS OF THE NUMBER OF SHARES YOU OWN.

IF YOU DO NOT ATTEND THE ANNUAL MEETING TO VOTE IN PERSON, YOUR VOTE WILL NOT BE
COUNTED UNLESS A PROXY REPRESENTING YOUR SHARES IS PRESENTED AT THE MEETING.

TO ENSURE THAT YOUR SHARES WILL BE VOTED AT THE ANNUAL MEETING, YOU SHOULD VOTE
VIA THE INTERNET, BY TELEPHONE OR BY MAIL WHETHER OR NOT YOU PLAN TO ATTEND THE
MEETING. IF YOU ATTEND THE ANNUAL MEETING, YOU MAY REVOKE YOUR PROXY AND VOTE
BY BALLOT.
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ROSLYN BANCORP, INC.

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

PROXY STATEMENT
ANNUAL MEETING OF STOCKHOLDERS
MAY 24, 2000

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Solicitation and Voting of Proxies

This Proxy Statement is being furnished to stockholders of Roslyn Bancorp,
Inc. ("Roslyn" or the "Company") in connection with the solicitation by the
Board of Directors of proxies to be used at the Annual Meeting of Stockholders
to be held on Wednesday, May 24, 2000, and at any adjournments of the Annual
Meeting. This Proxy Statement is first being mailed to record holders on or
about April 17, 2000.

Regardless of the number of shares of common stock owned, it is important
that holders of a majority of the shares be represented by proxy or in person at
the Annual Meeting. Please vote by completing the enclosed proxy card and
returning it signed and dated in the enclosed postage-paid envelope. Instead of
voting by proxy, stockholders of record can vote their shares over the Internet,
or by calling a specially designated telephone number. These new Internet and
telephone voting procedures are designed to authenticate stockholders'
identities, allow stockholders to provide their voting instructions and confirm
that their instructions have been recorded properly. Specific instructions for
stockholders of record who wish to use the Internet or telephone voting
procedures are set forth on the enclosed proxy card. Proxies solicited by the
Board of Directors will be voted in accordance with the directions given
therein. Where no instructions are indicated, signed and dated proxies will be
voted "FOR" each of the proposals presented in this Proxy Statement.

Other than the matters listed on the attached Notice of Annual Meeting of
Stockholders, the Board of Directors knows of no additional matters that will be
presented for consideration at the Annual Meeting. Execution of a proxy,
however, confers on the designated proxy holders discretionary authority to vote
the shares represented by proxy in their best judgment on such other business,
if any, that may properly come before the Annual Meeting and at any adjournments
of the Annual Meeting, including whether or not to adjourn the Annual Meeting.

You may revoke your proxy at any time before its exercise by filing a
written notice of revocation with the Corporate Secretary of the Company, by
delivering to the Company a duly executed proxy bearing a later date, or by
attending the Annual Meeting and voting in person. However, if you are a
stockholder whose shares are not registered in your own name, you will need
appropriate documentation from the holder of record to vote personally at the
Annual Meeting.

The cost of the solicitation of proxies on behalf of management will be
borne by the Company. In addition to the solicitation of proxies by mail and
through electronic means, Georgeson Shareholder Communications, Inc., a proxy
solicitation firm, will assist the Company in soliciting proxies for the Annual
Meeting and will be paid a fee of $8,000, plus out-of-pocket expenses. Proxies
may also be solicited personally, or by telephone, by Directors, officers and
other employees of the Company and its subsidiaries, without additional
compensation. The Company will also request persons, firms and corporations
holding shares in their names, or in the name of their nominees, which are
beneficially owned by others, to send proxy material to and obtain proxies from
such beneficial owners, and will reimburse such holders for their reasonable
expenses in doing so.
<PAGE>

If you are a registered stockholder, you can simplify your voting and save
the Company expense by voting via the Internet or calling the toll-free number
listed on the proxy card. Internet and telephone voting information is provided
on the proxy card. A Control Number, located on the lower right of the proxy
card, is designated to verify a stockholder's identity, allow the stockholder to
vote his or her shares, and confirm that the voting instructions have been
recorded properly. If you vote via the Internet, or by telephone, there is no
need to return a signed proxy card. If you choose not to vote via the Internet,
or by telephone, you may still vote by proxy by using the proxy card enclosed
with this Proxy Statement. Proxies submitted by Internet or by telephone voting
as described above must be received by 12:00 a.m. on May 23, 2000.

Voting Securities

The securities which may be voted at the Annual Meeting consist of shares
of common stock of the Company, with each share entitling its owner to one vote
on all matters to be voted on at the Annual Meeting, except as described below.
There is no cumulative voting for the election of Directors.

The Board of Directors has fixed the close of business on March 29, 2000 as
the record date (the "Record Date") for the determination of stockholders of
record entitled to notice of and to vote at the Annual Meeting, and at any
adjournments of the Annual Meeting. The total number of shares of common stock
outstanding and entitled to vote on the Record Date was 69,253,903 shares.

As provided in the Company's Certificate of Incorporation, record holders
of common stock who beneficially own in excess of 10% of the outstanding shares
of common stock (the "limit") are not entitled to any vote with respect to the
shares held in excess of the limit. A person or entity is deemed to
beneficially own shares owned by an affiliate of, as well as persons acting in
concert with, such person or entity. The Company's Certificate of Incorporation
authorizes the Board of Directors (1) to make all determinations necessary to
implement and apply the limit, including determining whether persons or entities
are acting in concert, and (2) to demand that any person who is reasonably
believed to beneficially own stock in excess of the limit supply information to
the Company to enable the Board of Directors to implement and apply the limit.

The presence, in person or by proxy, of the holders of at least a majority
of the total number of shares of common stock entitled to vote (after
subtracting any shares in excess of the limit pursuant to the Company's
Certificate of Incorporation) is necessary to constitute a quorum at the Annual
Meeting. If there are not enough votes to constitute a quorum, or to approve or
ratify any proposal at the time of the Annual Meeting, the Annual Meeting may be
adjourned in order to permit the further solicitation of proxies.

As to the election of Directors, the proxy card being provided by the Board
of Directors enables a stockholder to vote "FOR" the election of the nominees
proposed by the Board of Directors, or to "WITHHOLD" authority to vote for one
or more of the nominees being proposed. Under Delaware law and the Company's
Bylaws, Directors are elected by a plurality of votes cast, without regard to
either (1) broker "non-votes" or (2) proxies as to which authority to vote for
one or more of the nominees being proposed is withheld. A broker "non-vote"
occurs when a nominee holder of common stock for a beneficial owner does not
vote on a particular proposal because the nominee does not have discretionary
voting power with respect to that item and has not received instructions from
the beneficial owner.

As to the ratification of the appointment of KPMG LLP as independent
auditors of the Company and all other matters that may properly come before the
Annual Meeting, a stockholder may: (1) vote "FOR" the item; (2) vote "AGAINST"
the item; or (3) "ABSTAIN" from voting on such item. Under the Company's

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Bylaws, the affirmative vote of a majority of the votes cast at the Annual
Meeting is required to constitute stockholder ratification of the appointment of
KPMG LLP as independent auditors, and all other matters that may properly come
before the Annual Meeting. Accordingly, shares as to which the "ABSTAIN" box
has been selected on the proxy card will not be counted as votes cast and will
have no effect on the voting. Shares underlying broker non-votes, or in excess
of the limit, also will not be counted as votes cast and will have no effect.

Proxies solicited by means of this Proxy Statement will be returned to the
Company's transfer agent, Registrar and Transfer Company. The Board of
Directors has designated Registrar and Transfer Company to act as inspectors of
election and tabulate the votes at the Annual Meeting. Registrar and Transfer
Company is not otherwise employed by the Company or any of its affiliates.
After the final adjournment of the Annual Meeting, Registrar and Transfer
Company will return the proxies to the Company for safekeeping.

If you are a participant in The Roslyn Savings Bank Employee Stock
Ownership Plan, the Roslyn Bancorp, Inc. 1997 Stock-Based Incentive Plan, The
Roslyn Savings Bank 401(k) Plan or the T R Financial Corp. Employee Stock
Ownership Plan, you will receive separate proxy cards for the shares of common
stock credited to your account through each of those plans which will serve as a
voting instruction card for the trustees or administrators of those plans. If
you hold shares through any of these plans and do not vote, the respective plan
trustees will vote the shares in accordance with the terms of the respective
plans.

PROPOSALS TO BE VOTED ON AT THE ANNUAL MEETING

PROPOSAL 1. ELECTION OF DIRECTORS

The Board of Directors of the Company currently consists of 14 Directors
and is divided into three classes. Each member of the Company's Board of
Directors also serves as a Director of The Roslyn Savings Bank (the "Bank"),
which is a wholly owned subsidiary of the Company. Directors are elected for
staggered terms of three years each, with the term of office of only one class
expiring each year. Directors serve until their successors are elected and
qualified.

The five nominees proposed for election at this Annual Meeting are Thomas
J. Calabrese, Jr., Leonard Genovese, Dr. Edwin W. Martin, Jr., Spiros J.
Voutsinas and Richard C. Webel. Messrs. Voutsinas and Genovese are two of five
former directors of T R Financial Corp. and Roosevelt Savings Bank who were
appointed to the Board of Directors in February 1999 in accordance with the
terms of the Company's agreement to acquire T R Financial Corp. Under that
agreement, T R Financial Corp. selected five members of its Board of Directors,
who were approved by the Company, to become members of the Company's and the
Bank's Boards of Directors. As of February 16, 1999, the Boards of Directors of
the Company and the Bank were increased from 10 to 15 members to accommodate
these new Board members. These new members were placed within the three classes
of existing Directors. The three other former directors of the T R Financial
Corp. Board of Directors who were appointed to the Company's and the Bank's
Boards of Directors in February 1999 were John M. Tsimbinos, A. Gordon Nutt and
Maureen E. Clancy. Except as described above, no person being nominated as a
Director is being proposed for election pursuant to any agreement or
understanding between any such person and the Company. Effective December 31,
1999 , John P. Nicholson retired from the Board of Directors and the Board was
reduced to 14 members. Mr. Nicholson was elected to serve as a Director
Emeritus on the Company's and Bank's Boards of Directors.

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<PAGE>

Directors are elected by a plurality of votes cast. If any nominee is
unable to serve, or declines to serve for any reason, it is intended that the
proxies will be voted for the election of such other person as may be designated
by the Board of Directors. The Board of Directors has no reason to believe that
any of the persons named will be unable or unwilling to serve. Unless authority
to vote for the nominee is withheld, it is intended that the shares represented
by the enclosed proxy card, if executed, dated and returned, will be voted "FOR"
the election of the nominees proposed by the Board of Directors.

The Board of Directors recommends that you vote "FOR" the election of the
nominees named in this Proxy Statement.

Information with Respect to the Nominees, Continuing Directors and Certain
Executive Officers of the Company

The following table sets forth, as of the Record Date, certain information
regarding the nominees for Directors, continuing Directors and "Named Executive
Officers" of the Company. "Named Executive Officers" are all individuals who
have served either as the Company's Chief Executive Officer, or acted in a
similar capacity, during the last completed fiscal year, plus the Company's four
most highly compensated executive officers who received salary and bonus in
excess of $100,000, other than its Chief Executive Officer, and who were serving
as executive officers on December 31, 1999.

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Thomas J. Calabrese, Jr. 58 1994 2003 69,645 *
Vice President, Daniel Gale Agency, Inc.;
retired Managing Director - Human
Resources, NYNEX Corporation, a
telecommunications firm.

Spiros J. Voutsinas 66 1999 2003 123,826 *
Until the Company's acquisition of
T R Financial Corp. in February, 1999,
Mr. Voutsinas was a director of Roosevelt
Savings Bank since 1992 and a director of
T R Financial Corp. since 1993.
Mr. Voutsinas is President of Omega
Capital, Inc., a real estate development and
syndication firm, and a general partner of
Omega Partners LP, a money management
firm specializing in bank stocks. He is a
member of the board of the Hellenic
American Chamber of Commerce.
Mr. Voutsinas retired in 1988 as an
executive vice president and director of a
major New York savings institution with
over 28 years of experience in the banking
industry.

Leonard Genovese 65 1999 2003 145,141 *
Until the Company's acquisition of
T R Financial Corp. in February 1999,
Mr. Genovese was a director of Roosevelt
Savings Bank since 1992 and a director of
T R Financial Corp. since 1993.
Mr. Genovese also served as President and
Chief Executive Officer of Genovese Drug
Stores, Inc. He is a board member of St.
Christopher-Ottilie Services for Children and
Families, the National Association of Chain
Drug Stores, Kellwood Company, AID Auto
Stores, The Stephan Company and the
National Center for Disability Services.
</TABLE>

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<TABLE>
<CAPTION>
Amount
and Nature of Ownership
Expiration Beneficial as a
Name and Principal Occupation Director of Term as Ownership Percent
for Past Five Years Age Since(1) Director (2)(3)(4)(5)(6)(7)(8) of Class(9)
- ----------------------------- --- -------- -------- --------------------- -----------
<S> <C> <C> <C> <C> <C>
Dr. Edwin W. Martin, Jr. 68 1994 2003 72,063 *
President Emeritus and a director of the
National Center for Disability Services, a
non-profit education, rehabilitation and
research corporation since 1994. Before
1994, Dr. Martin was President and Chief
Executive Officer of the National Center for
Disability Services. Dr. Martin is a director
of the National Captioning Institute, a non-
profit agency, a director of Interboro Mutual
Indemnity Insurance Company, and a
director of Pall Corp., a manufacturer of
industrial filters.

Richard C. Webel 48 1995 2003 76,677 *
Managing Director, Innocenti & Webel, an
architectural firm. Mr. Webel is also
President of Webel Corporation, a strategic
planning company, and PlantAmerica, LLC,
a software development corporation.
Mr. Webel also serves as a general partner
of Roundbush Associates, a real estate
development corporation.

CONTINUING DIRECTORS:

Joseph L. Mancino 62 1991 2001 497,413 *
President and Chief Executive Officer of the
Company since 1996 and a Vice Chairman
of the Board of the Company since 1999;
Chairman of the Board and Chief Executive
Officer of the Bank since 1993.
Mr. Mancino was President of the Bank
from 1993 until February, 2000.
Mr. Mancino also serves as a director of the
Institutional Investors Mutual Fund, a
diversified open end mutual fund, the
Community Bankers Association of New
York State and the Savings Bank Life
Insurance Fund. Mr. Mancino has been a
Trustee of Long Island University since
1997. He has been a member of the Nassau-
Suffolk Advisory Board of Helen Keller
Services For The Blind - Long Island
Division since 1984 and has been a member
of the Board of Trustees of the National
Chapter since November 1990. Since 1995,
he has been a member of the Board of
Directors and Treasurer of the Interfaith
</TABLE>

6
<PAGE>

John M. Tsimbinos 62 1999 2001 2,877,080 4.1
Chairman of the Board of the Company and
Vice Chairman of the Board of the Bank
commencing in 1999. Until the Company's
acquisition of T R Financial Corp. in
February 1999, Mr. Tsimbinos had been the
Chairman of the Board and Chief Executive
Officer of Roosevelt Savings Bank since
1992. He also served as the Chairman of the
Board and Chief Executive Officer of T R
Financial Corp. since its inception in 1993.
He serves on various committees of the
Community Bankers Association of New
York State. Mr. Tsimbinos is a former
director of Institutional Investors Capital
Appreciation Fund, Inc. He also serves on
the board of Golden Eagle Sales Corp., a
wholly owned subsidiary of Columbian
Mutual Life Insurance Company, and the
advisory board of the Neighborhood
Housing Services of New York City, Inc.
Mr. Tsimbinos is a former director and Vice
Chairman of the Federal Home Loan Bank
of New York and a former Chairman of its
Executive Committee.

James E. Swiggett 68 1980 2001 125,630 *
Retired Chairman of the Board, President
and Chief Executive Officer of Kollmorgen
Corp., a diversified technology
manufacturing company.

Robert G. Freese 70 1988 2001 74,664 *
Retired Vice Chairman and Chief Financial
Officer of Grumman Corporation, a defense
contractor.
</TABLE>

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<PAGE>

<TABLE>
<CAPTION>
Amount
and Nature of Ownership
Expiration Beneficial as a
Name and Principal Occupation Director of Term as Ownership Percent
for Past Five Years Age Since(1) Director (2)(3)(4)(5)(6)(7)(8) of Class(9)
- ----------------------------- --- -------- -------- --------------------- -----------
<S> <C> <C> <C> <C> <C>
A. Gordon Nutt 65 1999 2001 732,265 1.0
Until his retirement in September 1999,
Mr. Nutt was Executive Vice President and
Special Transition Officer of the Company
and the Bank since February 1999. Until
the Company's acquisition of T R Financial
Corp. in February 1999, Mr. Nutt had been
President and Chief Administrative Officer
of Roosevelt Savings Bank since 1992, a
director of Roosevelt Savings Bank since
1991, and President, Chief Administrative
Officer and a director of T R Financial
Corp. since 1993.

John R. Bransfield, Jr. 58 1998 2002 247,893 *
A Vice Chairman of the Company
commencing in February 2000; President
and Chief Operating Officer of the Bank
commencing in February 2000.
Mr. Bransfield was Vice President of the
Company and Executive Vice President and
Senior Lending Officer of the Bank from
1996 until February 2000. Mr. Bransfield
was Senior Vice President and Senior
Lending Officer of the Bank from 1993 until
1996.

Thomas A. Doherty 62 1999 2002 9,500 *
Mr. Doherty is the Chief Administrative
Officer of First Quality Enterprises, Inc.,
Great Neck, New York, a manufacturer of
hygiene-related products. He is the retired
Chairman, President and Chief Executive
Officer of Fleet Bank and a member of the
Board of Directors of Long Island Power
Authority and of St. Joseph College in
Brooklyn, New York.

Maureen E. Clancy 67 1999 2002 132,627 *
Ms. Clancy was a director of Roosevelt
Savings Bank and T R Financial Corp. from
1993 until the Company acquired
T R Financial Corp. in February 1999. She
has been a licensed insurance broker since
1959. Ms. Clancy is the Secretary-Treasurer
of Clancy & Clancy Brokerage Ltd., an
insurance agency established in 1956.
</TABLE>

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<PAGE>

Victor C. McCuaig 71 1970 2002 81,980 *
Of counsel to and former partner in Payne,
Wood & Littlejohn, general counsel to the
Bank.

NAMED EXECUTIVE OFFICERS
WHO ARE NOT DIRECTORS:

Michael P. Puorro 40 -- -- 165,700 *
Treasurer and Chief Financial Officer of
the Company since 1996; Executive Vice
President and Chief Financial Officer of the
Bank commencing in 1999. Mr. Puorro
was a Senior Vice President and Chief
Financial Officer of the Bank from 1996
until 1999. From 1994 until 1996, he was
Vice President and Chief Financial Officer
of the Bank and before 1994 was Vice
President and Treasurer of the Bank.
Mr. Puorro has been employed by the Bank
since 1992.

John L. Klag 42 -- -- 154,952 *
Executive Vice President and Investment
Officer of the Bank commencing in 1999.
Mr. Klag was Senior Vice President and
Investment Officer of the Bank from 1996
until 1999. Before 1996, he was Vice
President and Investment Officer of the
Bank. Mr. Klag has been employed by the
Bank since 1993.

Directors and executive officers as a group -- -- -- 5,947,690(5)(6) 8.3%
(20 persons)
</TABLE>

_______________________________
* Represents less than 1.0% of the Company's outstanding common stock.
(1) Includes years of service as a Director of the Bank.
(2) The figures shown include unvested shares awarded under the Roslyn Bancorp,
Inc. 1997 Stock-Based Incentive Plan, as follows: Mr. Swiggett, 20,498
shares; Mr. Freese, 20,498 shares; Mr. Calabrese, 19,006 shares; Dr.
Martin, 19,006 shares; Mr. Webel, 19,006 shares; Mr. McCuaig, 20,610 shares;
and Mr. Doherty, 7,500 shares. Such shares are subject to awards which vest
at an annual rate of 20% and will have fully vested by February 19, 2003,
except for Mr. Doherty's shares, which will be fully vested on July 23,
2004. Each participant has voting, but not dispositive, power as to these
shares. See "Directors' Compensation --Stock-Based Benefits Plan."
(3) The figures shown include unvested shares awarded under the 1997 Stock-Based
Incentive Plan as follows: Mr. Mancino, 109,091 shares; Mr. Bransfield,
60,682 shares; Mr. Puorro, 37,500 shares; and Mr. Klag, 37,500 shares. A
portion of each award vests each year on September 2 and all such awards
will fully vest on September 2, 2002. The figures shown also include shares
awarded under the 1997 Stock-Based Incentive Plan (other than as reflected
in footnote 2) and which vest based upon the achievement of certain
specified performance objectives, but in no event later than September 2,
2002, as follows: Mr. Mancino, 30,000 shares; Mr. Bransfield, 13,333 shares;
Mr. Puorro, 6,267 shares; and Mr. Klag, 6,267 shares.

(Footnotes continued on following page)

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(4) The figures shown include shares as to which individuals have a right to
acquire beneficial ownership by the exercise of stock options, within 60
days of March 29, 2000, pursuant to the 1997 Stock-Based Incentive Plan
(and, in the case of Messrs. Tsimbinos, Nutt, Voutsinas and Genovese, and
Ms. Clancy, the T R Financial Corp. 1993 Incentive Stock Option Plan or the
T R Financial Corp. 1993 Stock Option Plan for Outside Directors) as
follows: Mr. Mancino, 199,827 shares; Mr. Bransfield, 112,141 shares; Mr.
Puorro, 68,577 shares; Mr. Klag, 68,577 shares; Mr. Tsimbinos, 1,065,109
shares; Mr. Nutt, 353,478 shares; Ms. Clancy, 52,414 shares; Mr. Voutsinas,
9,840 shares; Mr. Genovese, 93,829 shares, and Messrs. Calabrese, Freese,
Martin, McCuaig, Nicholson, Swiggett, Webel and York, 40,000 shares each;
and all Directors and executive officers, as a group, 2,409,946 shares.
(5) The figures shown include shares held in trust pursuant to The Roslyn
Savings Bank Employee Stock Ownership Plan (the "Roslyn ESOP") (and, in the
cases of Messrs. Tsimbinos and Nutt, the T R Financial Corp. Employee Stock
Ownership Plan and Trust, formerly sponsored by T R Financial Corp.) that
have been allocated, as of December 31, 1999, to individual accounts as
follows: Mr. Mancino, 4,423 shares; Mr. Bransfield, 4,005 shares; Mr.
Puorro, 3,935 shares; Mr. Klag, 3,779 shares; Mr. Tsimbinos, 59,190 shares;
Mr. Nutt, 59,190 shares; and all Directors (who are also employees) and
executive officers, as a group, 142,474 shares. Such persons have sole
voting power, but no investment power, except in limited circumstances, as
to such shares. The figures shown do not include 3,084,924 shares held in
trust pursuant to the Roslyn ESOP that have not been allocated to any
individual's account and as to which the members of the Roslyn ESOP
Committee (consisting of Mr. Mancino, Mr. Klag, Mr. Puorro and Mary Ellen
McKinley, the Bank's Human Resources Officer) disclaim beneficial ownership.
(6) The figures shown include shares held in the trust of the Roslyn 401(k) Plan
(and, in the case of Mr. Tsimbinos, the 401(k) plan formerly sponsored by
Roosevelt Savings Bank), as to which each person identified has shared
voting and investment power as follows: Mr. Mancino, 30,728 shares; Mr.
Bransfield, 4,614 shares; Mr. Puorro, 9,699 shares; Mr. Klag, 3,558 shares;
Mr. Tsimbinos, 128,172 shares; and all Directors (who are also employees)
and executive officers, as a group, 199,340 shares.
(7) The figures shown include shares over which individuals share voting and
investment power (other than as disclosed in Notes 4 and 5, above), as
follows: Mr. Mancino, 34,500 shares; Mr. Swiggett, 20,498 shares; Mr.
Calabrese, 500 shares; Dr. Martin, 100 shares; Mr. McCuaig, 4,000 shares;
Mr. Nicholson, 7,000 shares; Mr. Puorro, 100 shares; Mr. Klag, 2,500 shares;
Mr. Tsimbinos, 751,410 shares; Mr. Voutsinas, 8,766 shares; Ms. Clancy,
14,789 shares; Mr. Doherty, 1,500 shares; and all executive officers and
Directors, as a group, 840,475 shares.
(8) The figures shown include 17,935, 6,045, 1,823 and 1,739 shares over which
Messrs. Mancino, Bransfield, Puorro and Klag, respectively, have voting, but
not dispositive power, that are held in a trust account on their behalf
under The Roslyn Savings Bank Benefit Restoration Plan. The figure shown
includes 336,653 shares over which Mr. Tsimbinos has voting, but not
dispositive power, that are held in a trust account on his behalf under the
T R Financial Supplemental Executive Retirement Plan.
(9) Percentages with respect to each person, or group of persons, have been
calculated on the basis of 69,253,903 shares of Roslyn common stock, the
number of shares of Roslyn common stock outstanding and entitled to vote as
of March 29, 2000, plus the number of shares of Roslyn common stock which
such person or group of persons has the right to acquire within 60 days
after the Record Date by the exercise of stock options.

Section 16(a) Beneficial Ownership Reporting Compliance

Section 16(a) of the Securities Exchange Act of 1934, as amended (the
"Exchange Act"), requires the Company's executive officers and Directors, and
persons who own more than 10% of a registered class of the Company's equity
securities, to file reports of ownership and changes in ownership with the
Securities and Exchange Commission (the "SEC"). Executive officers, Directors
and greater than 10% stockholders are required by SEC regulation to furnish the
Company with copies of all Section 16(a) forms they file.

Based solely on a review of copies of such reports of ownership furnished
to the Company, or written representations that no forms were necessary, the
Company believes that during the past fiscal year, its executive officers,
Directors and greater than 10% beneficial owners complied with all applicable
filing requirements, except for Director Genovese, for whom an amended Form 3
was filed due to administrative error, and Director Voutsinas, for whom one
amended Form 3 and one amended Form 4 were filed due to administrative error.

10
<PAGE>

Meetings and Committees of the Boards of the Company and the Bank

The Board of Directors of the Company conducts its business through
meetings of the Board of Directors and through activities of its committees.
During fiscal 1999, the Board of Directors held 18 meetings. All of the
Directors of the Company attended at least 75% of the total number of the
Company's Board meetings held and committee meetings on which such Directors
served during fiscal 1999. The Board of Directors of the Company maintains
three committees as described below.

Audit Committee. The Audit Committee consists of Messrs. Freese, Swiggett,
Doherty, Genovese, Nutt and Webel, all of whom are outside Directors. The Audit
Committee reviews audit reports and management's actions regarding the
implementation of audit findings and reviews compliance with all relevant laws
and regulations. The Audit Committee performs the same functions as the
Examining Committee of the Bank and consists of the same Directors. The Audit
and Examining Committees each met four times in fiscal 1999.

Compensation Committee. The Compensation Committee consists of Messrs.
Calabrese, Freese, Swiggett, Martin and Webel, and Ms. Clancy. The Compensation
Committee establishes compensation and benefits for the executive officers and
reviews the incentive compensation programs when necessary. The Compensation
Committee is also responsible for establishing certain guidelines and limits for
compensation for other salaried officers and employees of the Company and the
Bank. In making determinations concerning compensation for officers and other
employees of the Company and the Bank, the Compensation Committee consults with
the Personnel Committee of the Bank, which consists of the same Directors who
are members of the Compensation Committee. In fiscal 1999, the Compensation
Committee met nine times and the Personnel Committee met eight times.

Nominating Committee. The Nominating Committee recommends persons to fill
vacancies on the Board of Directors and reviews the structure and operation of
the Board of Directors. The Nominating Committee consists of Messrs. Calabrese,
McCuaig and Swiggett. The Nominating Committee met two times in fiscal 1999.

Directors' Compensation

Directors' Fees. Each non-employee Director of the Company receives fees
of $1,850 per Board meeting attended and $900 per committee meeting attended,
unless such meetings are held consecutively with Board or committee meetings of
the Bank, in which case no fees are paid. Each non-employee Director of the
Bank receives fees of $1,850 per Board meeting attended and $900 per committee
meeting attended. In December 1999, the Board of Directors of the Company voted
to increase the fees for attendance at meetings of the Boards of Directors of
the Company and the Bank from $1,850 to $2,000 per meeting. Members of the
Advisory Board, which is comprised of the members of the former T R Financial
Corp. Board of Directors who did not become Directors of the Company or the
Bank, receive an annual retainer fee equal to the estimated average fees payable
during the year (including annual or retainer fees and fees for attending Board
or committee meetings) to a member of the Board of Directors for service on the
Company's Board of Directors. The function of the Advisory Board is to advise
the Company with respect to deposit and lending activities in T R Financial
Corp.'s former market area and to maintain and develop customer relationships.

11
<PAGE>

Stock-Based Benefits. On September 2, 1997, each outside Director of the
Company and the Bank was granted shares of restricted stock and options to
purchase Company common stock pursuant to the Company's 1997 Stock-Based
Incentive Plan, which began vesting in five equal installments on September 2,
1998. On February 19, 1998, each of the outside Directors of the Company and
the Bank on that date was granted shares of restricted stock and options to
purchase Company common stock under the Company's 1997 Stock-Based Incentive
Plan, which began vesting in five equal installments on February 19, 1999. The
exercise price related to the stock options granted in 1997 is $22.50 per share,
and $22.00 per share for options granted in 1998. Additionally, Thomas Doherty,
who became a Director on March 1, 1999, was awarded options to purchase 10,000
shares of the Company's common stock on July 23, 1999. The exercise price of
Mr. Doherty's stock options is $17.31 per share. The options also have limited
rights attached to them that provide for a cash payment to be made to the option
holder equal to the difference between the fair market value of the common stock
and the exercise price of the options in the event of a change in control. The
options expire 10 years after the date they were granted. All of the awards
become fully vested or exercisable upon the holders death, disability or
retirement, as well as upon a change in control. In addition, each outside
Director who was formerly a director of T R Financial Corp. holds options to
purchase shares of Company common stock that were granted pursuant to the T R
Financial Corp. 1993 Stock Option Plan for Outside Directors, which was assumed
by the Company in connection with its acquisition of T R Financial Corp. Each
of these options is fully exercisable and expires 10 years from the date of
grant, and has an exercise price ranging from $2.20 per share to $14.39 per
share.

Executive Compensation

The report of the Compensation Committee and the stock performance graph
shall not be deemed incorporated by reference by any general statement
incorporating by reference this Proxy Statement into any filing under the
Securities Act of 1933, as amended (the "Securities Act"), or the Exchange Act,
except to the extent that the Company specifically incorporates this information
by reference, and shall not otherwise be deemed filed under such Acts.

Compensation Committee Report on Executive Compensation. Under rules
established by the SEC, the Company is required to provide certain data and
information regarding the compensation and benefits provided to the Chief
Executive Officer and other executive officers of the Company and Bank for the
year ended December 31, 1999. Recommendations regarding all components of
compensation paid to executive officers of the Company and the Bank are made by
the Compensation Committee of the Company's Board of Directors and the Personnel
Committee of the Bank's Board of Directors, respectively, and are approved by
the appropriate Board. Neither the Company's nor the Bank's Board of Directors
rejected or modified, in any material way, any of the recommendations of the
Compensation Committee during fiscal 1999. Each member of the Compensation
Committee and the Personnel Committee is a non-employee Director.

For 1999, the Compensation Committee operated under a policy to structure
executive compensation in a manner intended to limit the likelihood that current
compensation would exceed the limits for deductibility prescribed by Section
162(m) of the Internal Revenue Code, as amended (the "Code"). This policy
continues in effect for fiscal 2000. However, the Compensation Committee
retains discretion to make future exceptions to this policy, and in determining
whether to do so, the Compensation Committee may consider a number of factors,
including but not limited to the Company's and the Bank's tax position, and the
materiality of amounts likely to be involved.

12
<PAGE>

Compensation Policies and Procedures. The Compensation Committee is
responsible for reviewing management's recommendations for compensation and
benefits for officers and employees, including officers and employees of the
Bank. It is the responsibility of the Compensation Committee to recommend to
the full Board of Directors the amount and composition of executive compensation
paid to the executive officers, including the President and Chief Executive
Officer. It is the responsibility of the Board of Directors to review and
consider such compensation recommendations of the Compensation Committee.

Management is faced continually with competitive and economic challenges.
The Compensation Committee believes that, if the Company is to be successful,
its compensation programs must be structured to attract and retain the highest
quality employees available. The Company's executive compensation programs are
intended to provide incentives that will reward managers for achieving superior
levels of performance which strengthen the Company and enhance stockholder
value.

The Compensation Committee annually reviews and evaluates base salary and
annual bonuses for all executive officers, and in conducting such reviews places
primary consideration upon the recommendations by the President and Chief
Executive Officer, along with the rationale for such recommendations, with the
exception of the compensation review of the President and Chief Executive
Officer. The President and Chief Executive Officer does not participate in the
Compensation Committee's decision as to his compensation package.

To achieve the compensation objectives established by the Compensation
Committee, the Company's executive compensation program consists of two main
elements, base salary and bonus, which comprise annual compensation. In
addition, executive officers participate in other benefit plans available to all
employees, including the retirement plan, the Roslyn ESOP, the 1997 Stock-Based
Incentive Plan, the Roslyn Bancorp, Inc. Annual Incentive Plan and the Roslyn
401(k) Plan, and may be selected to participate in supplemental benefit plans.

In establishing individual compensation levels, the Compensation Committee
considers the Company's overall objectives and performance, peer group
comparisons and individual performance. Except with respect to the
determination of bonus payments, as described below, no precise numerical
formula is used to determine an executive's salary. The Company's overall
performance and the achievement of financial and business objectives are
considered. Increases in compensation are recommended based on strong
individual performance in relationship to Company and individual goals.

To determine whether executive salary levels are within appropriate market
norms, the Compensation Committee examines and takes into account applicable
compensation levels among a representative peer group of financial services
institutions in the regional and local markets. For 1999, the Company engaged
William M. Mercer, Inc. ("Mercer"), a nationally-known employment consulting
firm, to provide it with current market data for compensation levels of
executive positions similar to those of the Company's executive officers and to
outline provisions for an annual incentive plan that would reinforce the
Company's pay-for-performance philosophy, tie incentive (variable) compensation
to the achievement of annual strategic and operating goals, and provide
competitive total cash compensation opportunities with upside (and downside)
potential. Mercer prepared a report (the "Mercer Report") benchmarking
compensation for the Company's selected executive positions based on data group
from 13 peer group savings banks in the New York Metropolitan area. Data was
collected according to functional responsibilities and rank to identify
compensation levels for peer group executives with comparable functions and rank
to the selected group of Company executives. In preparing its analysis, Mercer
relied

13
<PAGE>

upon its proprietary data collections as well as available published data,
including proxy information from similarly situated financial services
institutions operating in New York State, including the Metropolitan New York
City area, for information about comparable executive compensation levels.

The Mercer Report concluded that base salaries and total cash compensation
for the Company's executive officers holding the position of senior vice
president, or above, generally were well below both those of executive officers
in the Company's peer group and the market median. The Mercer Report found that
the average base salary paid to the Company's senior executives was 22% less
than the peer group median and 39% less than the seventy-fifth percentile for
the peer group. In terms of total cash compensation, the Mercer Report found
that amounts paid to the Company's senior executive officers were 25% less than
the peer group median and 50% less than the peer group's seventy-fifth
percentile. With respect to vice president positions, the Mercer Report
concluded that overall base salaries were, well below the market median, annual
incentive targets were at or below the market median and overall total cash
compensation, was well below the market median. The Mercer Report showed that
base salaries were 26% less than the peer group median and 42% less than the
peer group's seventy-fifth percentile, and total cash compensation for these
officers was 31% less than the peer group median and 64% less than the seventy-
fifth percentile.

Based on the conclusions and recommendations in the Mercer Report, the
Compensation Committee determined that an adjustment was needed to bring the
Company's executive compensation levels into line with the Company's peers in
order to maintain and attract talented personnel. The Compensation and
Personnel Committees recommended, and the Boards of Directors of the Company and
the Bank approved, increases in the base salary levels for the Bank's senior
executive officers, bringing them in line with the industry median. Most
executives who received such increases still fall well below the seventy-fifth
percentile. Salaries for the Named Executives Officers were increased to the
amounts shown in the summary compensation table shown on page 17.

Base Salaries. Salaries recommended by the Compensation Committee are
intended to be consistent and competitive with the practices of comparable
financial services institutions and each executive's level of responsibility.
The Compensation Committee generally utilizes internal and/or external surveys
of compensation paid to executive officers performing similar duties for
depository institutions and their holding companies with particular focus on the
level of compensation paid by comparable peer institutions. Adjustments also
reflect the performance of the executive and any increased responsibility
assumed by the executive.

Bonus. To secure the deductibility of bonuses awarded to executive
officers, bonuses for 1999 were awarded under the Roslyn Bancorp, Inc. Annual
Incentive Plan, which was approved by stockholders in 1999. The Annual
Incentive Plan establishes certain performance criteria for determining bonuses
for eligible employees. The maximum annual payment to any individual under the
plan is $1.5 million.

Under the Company's Annual Incentive Plan, the Board established bonus
levels for Company employees based on the Company's achievement of core earnings
per share. In order to tie employee incentive compensation to stockholder
interests, it was determined that increasing levels of incentive awards would be
paid for increasing levels of core earnings achieved by the Company. Core
earnings of $105.0 million, for example, would result in a 17.5% bonus being
paid to eligible Bank employees. In September 1999, the Bank determined that
core earnings for the year would likely exceed $100 million, and, therefore, a
15% performance-based bonus was paid to all employees below the level of
Executive Vice

14
<PAGE>

President. The Board adopted an additional scaled bonus structure tied to
Company earnings for those employees at the level of Senior Vice President and
higher. Varying percentage bonuses were to be paid upon the Company's attainment
of increasing levels of core earnings, with the Chief Executive Officer
receiving the highest percentage bonus and others receiving incrementally less.

Based on the Company's final determination that core earnings were $104.5
million for 1999 in accordance with the formula adopted earlier in the year, the
Board of Directors determined that all employees should be paid an additional
2.5% incentive bonus in addition to the 15% bonus already declared, with members
of the Company's senior management receiving their bonuses in 2000.
Additionally, as a result of the Company having achieved core earnings of $104.5
million in 1999, it was determined that senior management was entitled to an
additional bonus as indicated on the summary compensation table at page 17.

Chief Executive Officer Compensation. The compensation of the Chief
Executive Officer during 1999 consisted of the same elements as for other senior
executives, including base salary and bonus. The Compensation Committee set Mr.
Mancino's base salary at $562,000 effective April 1, 1999. This represents an
increase of $52,000, or 10%, over his 1998 base salary. In establishing his
base salary, the Committee reviewed Mr. Mancino's performance for the prior year
and also considered the Company's financial and business performance, including
net income and profitability, as well as the total cash compensation paid to
chief executive officers of similarly situated peer financial services
institutions as reflected in the Mercer Report. The Mercer Report concluded
that the base pay of the Company's Chief Executive Officer was well below that
of the peer group institutions surveyed, and recommended his salary be
increased. The Compensation Committee did not assign weights or ranking to
factors regarding this performance, but instead made subjective determinations
based on consideration of all related factors in the Company's business
performance.

As noted above, Mr. Mancino was also paid a discretionary cash bonus of
$632,060 for fiscal 1999. The Compensation Committee, in determining an
appropriate 1999 bonus for Mr. Mancino, considered his leadership of the Company
and the continued success of the Bank, as demonstrated by, among other things,
continued strong earnings and other criteria as discussed above. The bonus paid
to Mr. Mancino was made in accordance and consistent with the Annual Incentive
Plan adopted in 1999 and the criteria set by the Board of Directors thereunder
in view of bonus compensation paid to chief executive officers of similarly
situated peer financial services institutions.

The Compensation Committee

Thomas J. Calabrese, Jr.
Maureen E. Clancy
Robert G. Freese (Chairman)
Dr. Edwin W. Martin, Jr.
James E. Swiggett
Richard C. Webel

15
<PAGE>

Stock Performance Graph. The following graph shows a comparison of total
stockholder return on the Company's common stock, based on the market price of
the common stock with the cumulative total return of companies in The Nasdaq
Market Index and the MG Index for Savings and Loans for the period beginning on
January 13, 1997, the date Roslyn common stock began trading on the Nasdaq Stock
Market, through December 31, 1999. The graph may not be indicative of possible
future performance of the Company's common stock. The data was supplied by
Media General Financial Services.

COMPARATIVE TOTAL RETURNS

[GRAPH APPEARS HERE]

<TABLE>
<S> <C> <C> <C> <C>
01/13/97 12/31/97 12/31/98 12/31/99
--------- --------- --------- ---------

Roslyn Bancorp, Inc. ............ $100.00 $234.56 $221.11 $195.82
Nasdaq Market Index.............. 100.00 122.32 172.52 304.29
MG Index for Savings and Loans... 100.00 168.14 147.39 118.49
</TABLE>

Notes:
- -----
A. The lines represent monthly index levels derived from compounded daily
returns that include reinvestment of all dividends.
B. The indexes are re-weighted daily using the market capitalization on the
previous trading day.
C. If the monthly interval, based on the fiscal year-end, is not a trading
day, the preceding trading day is used.
D. Each index was set to $100.00 on January 13, 1997, the first day of trading
for Roslyn Bancorp, Inc. common stock. For Roslyn Bancorp, Inc. the index
commenced with the closing price on the first day of trading, which was
$15.00 per share.

16
<PAGE>

Summary Compensation Table. The following table sets forth the cash
compensation paid by the Bank, as well as certain other compensation paid or
accrued for services rendered in all capacities during the years ended December
31, 1999, 1998 and 1997, to the Chief Executive Officer and the Named Executive
Officers. Mr. Tsimbinos became Chairman of the Board of Directors of the
Company on February 16, 1999. Therefore, his compensation is included in this
table for 1999.

<TABLE>
<CAPTION>
Long-Term
Annual Compensation(1) Compensation Awards
---------------------------------- -----------------------------
OTHER SECURITIES
ANNUAL RESTRICTED UNDERLYING ALL OTHER
SALARY BONUS COMPENSATION STOCK AWARDS OPTIONS/SARS COMPENSATION
NAME AND PRINCIPAL POSITIONS YEAR ($) ($) ($)(2) ($)(3) (#) ($)(4)(5)(6)
- ---------------------------- ---- -------- --------- ------------ ------------ -------------- ------------
<S> <C> <C> <C> <C> <C> <C> <C>
Joseph L. Mancino................. 1999 $562,000 $632,060 $ -- $ -- -- $ 209,474
Vice Chairman of the Board of 1998 515,385 $260,000 -- -- -- 299,757
Directors, President and Chief 1997 497,692 2,500 -- 5,273,519 518,545 180,002
Executive Officer

John M. Tsimbinos................. 1999 $438,023 $ 75,668 $ -- $ -- -- $ 182,491
Chairman of the Board of
Directors

John R. Bransfield, Jr. .......... 1999 $275,846 $253,400 $ -- $ -- -- $ 100,223
Vice Chairman of the Company; 1998 259,692 104,800 -- -- -- 125,419
President and Chief Operating 1997 258,462 1,500 -- 2,816,459 288,841 78,813
Officer of the Bank

Michael P. Puorro................. 1999 $186,823 $137,191 $ -- $ -- -- $ 63,058
Executive Vice President and 1998 151,538 53,580 -- -- -- 65,936
Chief Financial Officer of the 1997 150,769 400 -- 1,671,675 175,334 43,826
Bank

John L. Klag...................... 1999 $176,777 $130,227 $ -- $ -- -- $ 53,070
Executive Vice President and 1998 141,431 50,000 -- -- -- 63,427
Investment Officer of the Bank 1997 140,673 300 -- 1,671,675 175,334 40,715
</TABLE>

_________________________________
(1) Under Annual Compensation, the column titled "Salary" includes deferred
amounts under the Bank's 401(k) Plan and the column titled "Bonus" consists
of cash bonuses, attendance bonuses, loan referral bonuses and recruitment
bonuses.
(2) For 1999, 1998 and 1997, there were no: (a) perquisites over the lesser of
$50,000 or 10% of the individual's total salary and bonus for the year; (b)
payments of above-market preferential earnings on deferred compensation; (c)
payments of earnings with respect to long-term incentive plans before
settlement or maturation; (d) tax payment reimbursements; or (e)
preferential discounts on stock.
(3) Represents Stock Awards granted under the 1997 Stock-Based Incentive Plan
consisting of 181,818, 101,138, 62,500 and 62,500 shares awarded to Messrs.
Mancino, Bransfield, Puorro and Klag, respectively, which began vesting in
five equal annual installments on September 2, 1998, and 45,000, 20,000,
9,400 and 9,400 shares awarded to Messrs. Mancino, Bransfield, Puorro and
Klag, respectively, which will vest not later than September 2, 2002, but
may vest earlier based on the achievement of certain specified performance
objectives. When shares vest and are distributed, the recipients will also
receive an amount equal to the accumulated cash and stock dividends paid
with respect thereto, plus earnings thereon. As of December 31, 1999, the
market value of the 139,090, 74,015, 43,766, and 43,766 unvested shares
awarded to Messrs. Mancino, Bransfield, Puorro and Klag was $2,573,165,
$1,369,277, $809,671 and $809,671, respectively, based on a closing stock
price of $18.50 per share.
(4) For 1999, such amounts include: (a) $7,686, $4,956, $876 and $827 of imputed
income from group term life insurance on behalf of Messrs. Mancino,
Bransfield, Puorro and Klag, respectively. With respect to Messrs Mancino,
Bransfield, Puorro and Klag, the figures shown also include $32,000, $3,023,
$3,528 and $1,646, respectively, reimbursed to each person for unused
vacation. For Mr. Tsimbinos, such amount includes a $153,473 payment
pursuant to the non-competition provisions of his employment agreement and
$15,032 in 401(k) and 401(k) excess benefit plan matching.
(5) For 1999, the figures shown include $23,976, $13,986, $23,976, $22,773 and
$20,868 for Messrs. Mancino, Tsimbinos, Bransfield, Puorro and Klag,
respectively, which represents the value of allocations made under the
Roslyn ESOP.
(6) For 1999, such amounts include $145,812, $68,268, $35,831 and $29,729 for
Messrs. Mancino, Bransfield, Puorro and Klag, respectively, which represents
the value of contributions made under the Roslyn Savings Bank Benefit
Restoration Plan.

17
<PAGE>

Employment Agreements

The Company and the Bank have entered into employment agreements with each
of the Named Executive Officers. The Company and the Bank intend for the
employment agreements to ensure that the management base of the Company and the
Bank remains stable. The continued success of the Company and the Bank depend
to a significant degree on the skills and competence of the Named Executive
Officers.

Each of the employment agreements, other than those entered into with Mr.
Tsimbinos, provide for a five-year term of employment that extends on a daily
basis until either the executive or the Company or the Bank, as applicable,
provides written notice of non-renewal, at which time the term of the agreements
becomes a fixed five-year term. The employment agreements with Mr. Tsimbinos,
which were entered into by the Company and the Bank, respectively, in connection
with the acquisition of T R Financial Corp. and Roosevelt Savings Bank, provide
for terms of employment that expire on June 30, 2002.

Under the employment agreements, the annual salary of each of the Named
Executive Officers, except Mr. Tsimbinos, is reviewed annually by the Board of
Directors or a committee of the Board of Directors. For 2000, the annual salary
for each of Messrs. Mancino, Bransfield, Puorro, and Klag has been set at
$650,000, $370,000, $220,000, and $210,000, respectively. The employment
agreements for Mr. Tsimbinos provides for an annual rate of salary equal to the
greater of (1) $500,000 or (2) the annual rate of salary for the second highest
paid employee of the Company or the Bank, taking into account all forms of cash
compensation. In addition to an annual salary, the employment agreements
provide for, among other things, participation in stock benefit plans and other
certain employee and fringe benefit programs applicable to executive management.
In addition to these items, the employment agreements for Mr. Tsimbinos provide
for the annual payment of $175,000 in exchange for Mr. Tsimbinos' agreement not
to compete with the Company or the Bank for one year following his termination
with the Company or the Bank upon certain circumstances. The employment
agreements with Mr. Tsimbinos also provide that the aggregate present value of
the compensation and benefits provided to him each year shall equal $1,000,000.

Each of the employment agreements provides that the Company, or the Bank,
may terminate the covered executive for cause, as described in the agreements,
at any time. If either the Company, or the Bank, terminate an executive's
employment other than for cause or in the event the executive terminates his
employment with the Company or the Bank upon any (1) notice to the executive of
non-renewal of the term of the agreement (except in the case of Mr. Tsimbinos);
(2) failure to elect or reelect or appoint or reappoint the executive to his
current positions; (3) material change in the executive's functions, duties or
responsibilities which cause the executive's position to become one of lesser
responsibility, importance or scope; (4) relocation of the executive's principal
place of employment by more than 25 miles; (5) reduction in the benefits or
perquisites provided to the executive; (6) liquidation or dissolution of the
Company or the Bank; or (7) breach of the agreement by the Company or the Bank,
the executive or, in the event of the executive's death, his beneficiary will
receive the payments and benefits that would have been provided to the executive
under the agreement for the remaining term of the agreement.

Under each of the employment agreements if, following a change in control
of the Company or the Bank, the executive's employment with the Company or the
Bank involuntarily terminates, the executive (other than Mr. Tsimbinos)
voluntarily terminates his employment for any reason within 60 days following
the change in control or the executive voluntarily terminates his employment at
any time during the term of the agreement as a result of any demotion, loss of
title, office or significant authority or relocation of his principal place of
employment by more than 25 miles, the executive (other than Mr. Tsimbinos) or,
in the event of the executive's death, his beneficiary, will receive an amount
equal to the greater of (1) the

18
<PAGE>

payments due for the remaining term of the agreement or (2) the greater of (a)
five times the executive's average annual compensation for the three preceding
taxable years or (b) five times the executive's annual compensation for the last
preceding taxable year. In addition, the executive will be provided with health
and welfare benefits for 60 months following his termination of employment. The
severance payment due Mr. Tsimbinos in connection with his qualifying
termination from of employment in connection with a change in control generally
equals the greater of (1) the payments due for the remaining term of the
agreement or (2) three times his annual compensation for the most recently
completed year. Notwithstanding that both the Company and the Bank employment
agreements provide for payments and benefits to the executives in connection
with a change in control, the executive would not receive duplicative payments
and benefits under the agreements.

Payments pursuant to the employment agreements and other arrangements in
the event of a change in control may constitute a "parachute payment" for
federal income tax purposes and may result in the imposition of an excise tax on
the executive. In such a case, the employment agreements provide that the
Company or the Bank will pay the executive an amount sufficient to enable the
executive to retain the payments and benefits provided to him had he not been
subject to such a tax.

The Company guarantees the payment of compensation and benefits to the
executives under the employment agreements with the Bank. The Company will also
make all payments to the executives under the employment agreements with the
Company. The Company and the Bank will reimburse or pay the executive for all
reasonable costs and legal fees paid or incurred in connection with any dispute
or question of interpretation relating to the employment agreements if the
executive is successful on the merits of his claim pursuant to a legal judgment,
arbitration or settlement.

Stock Option Grants

As discussed below and as an inducement to attract and retain qualified
directors, officers and employees, the Company maintains the Roslyn Bancorp,
Inc. 1997 Stock-Based Incentive Plan (the "Incentive Plan") and has assumed the
T R Financial Corp. 1993 Incentive Stock Option Plan and the T R Financial Corp.
1993 Stock Option Plan for Outside Directors. There were no grants of options
under any of these plans to the Named Executive Officers for 1999.

19
<PAGE>

AGGREGATED OPTION/SAR EXERCISES IN LAST FISCAL YEAR
AND FISCAL YEAR-END OPTION/SAR VALUES

The following table provides certain information with respect to the number
of shares of common stock represented by outstanding options held by the Named
Executive Officers as of December 31, 1999.

<TABLE>
<CAPTION>
Shares
Acquired Number Of Securities Value Of Unexercised
on Value Underlying Unexercised In-the-Money Options/SARs
Exercise(#) Realized($) Options/SARs at FY-End (#) at FY-End ($)(1)
-------------------------- -------------------------- --------------------------------
Name Exercisable Unexercisable Exercisable Unexercisable
- ---------------------- ------------- ------------ -------------------------- --------------- ---------------
<S> <C> <C> <C> <C> <C> <C>
Joseph L. Mancino......... -- $ -- 199,827 318,718 $ -- $ --
John M. Tsimbinos......... 252,073 4,049,466 1,065,109 -- 14,649,243 --
John R. Bransfield, Jr. .. -- -- 112,141 176,700 -- --
John L. Klag.............. -- -- 68,577 106,757 -- --
Michael P. Puorro......... -- -- 68,577 106,757 -- --
</TABLE>

________________________________
(1) Options are considered "in-the-money" only if the market price exceeds the
exercise price. The exercise price of each option is the fair market value
of the stock as of the date of the grant, i.e., $22.50 per share, except for
Mr. Tsimbinos whose exercise prices are $2.20 per share (for 770,934 shares
underlying options with an expiration date of June 29, 2003), $8.23 per
share (for 143,500 shares underlying options with an expiration date of June
29, 2007), $14.39 per share (for 150,675 shares underlying options with an
expiration date of January 23, 2007), and $14.39 per share (for 150,675
shares underlying options with an expiration date of January 22, 2008). The
closing price of Roslyn's common stock as of December 31, 1999 was $18.50
per share. The options consist of 404,545, 237,841, 151,934 and 151,934
incentive and non-statutory stock options granted to Messrs. Mancino,
Bransfield, Klag and Puorro, respectively, which began vesting at an annual
rate of 20% beginning September 2, 1998, and 114,000, 51,000, 23,400 and
23,400 options granted to Messrs. Mancino, Bransfield, Klag and Puorro,
respectively, which vest in installments based upon the achievement of
certain specified performance objectives, but in no event later than
September 2, 2002. The options will expire 10 years from the date of grant.
(2) The Incentive Plan generally provides for the grants of options to purchase
common stock of Roslyn Bancorp, Inc. at prices not less than the fair market
value of the stock on the date of grant, as well as certain related rights.
Awards granted under the Incentive Plan may be subject to certain
performance criteria established by the administering committee. Options
granted under the Incentive Plan have terms of not greater than 10 years.
The administering committee determines the terms and conditions of awards
granted under the Incentive Plan. However, by operation of the plan, all
awards immediately become vested and exercisable upon a change in control of
the Company or the Bank and upon the death or disability of a participant.
The committee may also accelerate the vesting on exercisability of awards in
the event of a participant's retirement.

Retirement Plan. The Bank maintains a defined benefit plan ("Retirement
Plan") for eligible employees. The Retirement Plan is intended to satisfy the
requirements of Section 401(a) of the Code. Eligible employees generally begin
participating in the Retirement Plan on the first day of the calendar month
coincident with or next following the date on which they have attained age 21
and have completed at least one year of service with the Bank. All employees
are eligible to participate in the Retirement Plan other than: (1) employees
paid on an hourly-rate or contract basis; (2) employees regularly employed
outside the Bank's own offices in connection with the operation and maintenance
of building and other property acquired through foreclosure or deed; and (3)
leased employees. Participants become vested in their benefits under the
Retirement Plan upon completing five years of vesting service.

The Retirement Plan provides for a monthly benefit to a participant upon
retirement at or after the later of (1) attainment of age 65 or (2) the fifth
anniversary of initial participation in the Retirement Plan. The Retirement Plan
also provides for a benefit upon the participant's death or early retirement.
The annual normal retirement benefit for a participant under the Retirement Plan
is (a) 2% of average annual earnings multiplied by years of credited service (up
to a maximum of 30 years), plus (b) 0.5% of average annual earnings multiplied
by the participant's number of years and months of credited service in excess of
30 years.

20
<PAGE>

For purposes of the Retirement Plan, average annual earnings means the
participant's average annual compensation (as defined in the Retirement Plan)
during the 36 consecutive calendar months within the final 120 consecutive
calendar months of the participant's credited service that yields the highest
average. A participant is eligible to receive an early retirement benefit upon
the completion of at least 10 consecutive years of vested service in the
Retirement Plan and (1) attainment of age 60, or (2) the sum of the
participant's age and years of service equals at least 75. Benefits are
generally paid in a straight life annuity for unmarried participants and in the
form of a 50% joint and survivor annuity (with the spouse as designated
beneficiary) for married participants. Other forms of benefit payments are
available under the Retirement Plan.

Benefit Restoration Plans. The Bank maintains a Benefit Restoration Plan
(the "BRP"), a non-qualified plan designed to permit certain employees to
receive supplemental retirement income from the Bank. Participants in the BRP
generally receive a benefit equal to the amount the participant would have
received under the ESOP, 401(k) Plan and the Retirement Plan, but for
limitations imposed on such benefits by certain provisions of the Code. The BRP
is an unfunded plan, which provides participants only with a contractual right
to obtain the benefits provided thereunder from the general assets of the Bank.
For fiscal 1999, Messrs. Mancino, Bransfield, Puorro and Klag participated in
the BRP. Mr. Tsimbinos participated in a similar plan sponsored by T R
Financial Corp. and, by the terms of his employment agreements, is entitled to
supplemental pension benefits.

ESTIMATED ANNUAL BENEFITS UNDER THE RETIREMENT PLAN AND THE BRP

The following table sets forth the estimated annual benefits payable under
the Retirement Plan upon a participant's retirement at age 65 for the year ended
December 31, 1999, expressed in the form of a straight life annuity, and any
related amounts payable under the BRP. The covered compensation under the
Retirement Plan and BRP includes the base salary for participants and does not
consider cash bonuses. The benefits listed in the table below for the
Retirement Plan and BRP are not subject to a reduction for social security
benefits or any other offset amount.

<TABLE>
<CAPTION>
Final Average Years Of Service
----------------------------------------------------------------------
Compensation 15 20 25 30 35 40
- ------------- ---------- ---------- ---------- ---------- ---------- ----------
<S> <C> <C> <C> <C> <C> <C>
$ 50,000 $ 15,000 $ 20,000 $ 25,000 $ 30,000 $ 31,250 $ 32,500
100,000 30,000 40,000 50,000 60,000 62,500 65,000
125,000 37,500 50,000 62,500 75,000 78,125 81,250
150,000 45,000 60,000 75,000 90,000 93,750 97,500
175,000 52,500 70,000 87,500 105,000 109,375 113,750
200,000 60,000 80,000 100,000 120,000 125,000 130,000
225,000 67,500 90,000 112,500 135,000 140,625 146,250
250,000 75,000 100,000 125,000 150,000 156,250 162,500
300,000 90,000 120,000 150,000 180,000 187,500 195,000
350,000 105,000 140,000 175,000 210,000 218,750 227,500
400,000 120,000 160,000 200,000 240,000 250,000 260,000
450,000 135,000 180,000 225,000 270,000 281,250 292,500
500,000 150,000 200,000 250,000 300,000 312,500 325,000
550,000 165,000 220,000 275,000 330,000 343,750 357,500
600,000 180,000 240,000 300,000 360,000 375,000 390,000
650,000 195,000 260,000 325,000 390,000 406,250 422,500
700,000 210,000 280,000 350,000 420,000 437,500 455,000
</TABLE>

21
<PAGE>

The approximate years of service, as of December 31, 1999, for the Named
Executive Officers are as follows:

Years Of
Service
----------
Joseph L. Mancino........................ 39
John M. Tsimbinos........................ 18
Michael P. Puorro........................ 7
John L. Klag............................. 7
John R. Bransfield, Jr. ................. 7

Management Supplemental Executive Retirement Plan. The Bank also sponsors
a non-qualified management supplemental executive retirement plan (the "MSERP")
to provide eligible employees with additional retirement benefits. The MSERP
benefit is intended to make up for benefits lost under the ESOP allocation
procedures to participants who retire before the complete repayment of the ESOP
loan. At the retirement of a participant, the benefits under the MSERP are
determined by: (1) projecting the number of shares that would have been
allocated to the participant under the ESOP if they had been employed throughout
the period of the ESOP loan (measured from the participant's first date of ESOP
participation); (2) reducing that number determined by the number of shares
actually allocated to the participant's account under the ESOP; and (3)
multiplying the resulting number of shares by the average fair market value of
the common stock over the preceding five years. Benefits under the MSERP
generally vest in 20% annual increments over a five year period commencing as of
the date of a participant's participation in the MSERP. The vested portion of
the MSERP participant's benefits are payable upon the retirement of the
participant.

Transactions With Certain Related Persons

The Bank's policies do not permit the Bank to make loans to any of its
Directors and executive officers. The Company intends that all transactions
between the Company and its executive officers, Directors, holders of 10% or
more of the shares of any class of its common stock and affiliates thereof, will
contain terms no less favorable to the Company than could have been obtained by
it in arm's length negotiations with unaffiliated persons and will be approved
by a majority of independent outside Directors of the Company not having any
interest in the transaction.

During 1999, Victor McCuaig, one of the Company's Directors, was of counsel
to the law firm of Payne, Wood & Littlejohn. Payne, Wood & Littlejohn furnished
the Bank with certain legal services. The fees that were paid by the Bank for
these legal services was approximately $608,000.

22
<PAGE>

PROPOSAL 2. RATIFICATION OF APPOINTMENT
OF INDEPENDENT AUDITORS

The Company's independent auditors for the fiscal year ended December 31,
1999 were KPMG LLP. The Company's Board of Directors has reappointed KPMG LLP to
continue as independent auditors for the Bank and the Company for the year
ending December 31, 2000, subject to ratification of such appointment by the
stockholders. If stockholders do not ratify the appointment of KPMG LLP as
independent auditors, the Board of Directors may consider other independent
auditors.

Representatives of KPMG LLP will be present at the Annual Meeting. They
will be given an opportunity to make a statement if they desire to do so and
will be available to respond to appropriate questions from stockholders present
at the Annual Meeting.

Unless marked to the contrary, the shares represented by the enclosed proxy
card will be voted "FOR" ratification of the appointment of KPMG LLP as the
independent auditors of the Company.

The Board of Directors recommends that you vote "FOR" ratification of the
appointment of KPMG LLP as the independent auditors of the Company.

ADDITIONAL INFORMATION

Stockholder Proposals

To be considered for inclusion in the Company's proxy statement and form of
proxy relating to the 2001 Annual Meeting of Stockholders, which is anticipated
to be held on May 23, 2001, a stockholder proposal must be received by the
Corporate Secretary of the Company at the address set forth on the first page of
this Proxy Statement not later than December 18, 2000. Any such proposal will
be subject to SEC Rule 14a-8.

Notice of Business to be Conducted at an Annual Meeting

The Bylaws of the Company provide an advance notice procedure for certain
business to be brought before an annual meeting. In order for a stockholder to
properly bring business before an annual meeting, the stockholder must give
written notice to the Secretary of the Company not less than 90 days before the
time originally fixed for such meeting; provided, however, that in the event
that less than 100 days' notice or prior public disclosure of the date of the
meeting is given or made to stockholders, notice by the stockholder to be timely
must be received not later than the close of business on the tenth day following
the day on which such notice of the date of the annual meeting was mailed or
such public disclosure was made. In order for the notice of a stockholder
proposal for consideration at the Company's 2001 Annual Meeting of Stockholders
to be timely, the Company would have to receive such notice no later than
February 12, 2001 assuming the 2001 Annual Meeting is held on May 23, 2001 and
that the Company provides at least 100 days' notice or public disclosure of the
date of the meeting. The notice must include the stockholder's name and
address, as it appears on the Company's record of stockholders, a brief
description of the proposed business, the reason for conducting such business at
the annual meeting, the class and number of shares of the Company's common stock
that are beneficially owned by such stockholder and any material interest of
such stockholder in the proposed business. In the case of nominations to the
Board, certain information regarding the nominee must be provided. Nothing in
this paragraph shall be deemed to require the Company

23
<PAGE>

to include in its proxy statement and proxy relating to an annual meeting any
stockholder proposal which does not meet all of the requirements for inclusion
established by the SEC in effect at the time such proposal is received.

A copy of the full text of the Bylaw provisions discussed above may be
obtained by writing to the Corporate Secretary at 1400 Old Northern Boulevard,
Roslyn, New York 11576.

Roslyn's Annual Report on Form 10-K for the fiscal year ended December 31,
1999, as well as the 1999 Annual Report to Stockholders, may be accessed through
the Company's world wide web site (www.roslyn.com). A copy of the Form 10-K is
available without charge upon written request to Ms. Mary Feder, Director of
Investor Relations, Roslyn Bancorp, Inc., 1400 Old Northern Boulevard, Roslyn,
New York 11576. Such request must include a good faith representation that, as
of March 29, 2000, the person making such request was a beneficial owner of
shares of common stock.

Other Matters Which May Properly Come Before the Annual Meeting

The Board of Directors knows of no business which will be presented for
consideration at the Annual Meeting other than as stated in the Notice of Annual
Meeting of Stockholders. If, however, other matters are properly brought before
the Annual Meeting, it is the intention of the persons named in the accompanying
proxy to vote the shares represented thereby on such matters in accordance with
their best judgment.

Whether or not you intend to be present at the Annual Meeting, please
return your proxy card promptly or vote your proxy using our telephone or
Internet voting resources as described on the proxy card. If you are then
present at the Annual Meeting and wish to vote your shares in person, your
original proxy may be revoked by voting at the Annual Meeting.

By Order of the Board of Directors

/s/ R. Patrick Quinn
R. Patrick Quinn
Corporate Secretary

Roslyn, New York
April 17, 2000

YOU ARE CORDIALLY INVITED TO ATTEND THE ANNUAL MEETING IN PERSON. WHETHER
OR NOT YOU PLAN TO ATTEND THE ANNUAL MEETING, YOU ARE REQUESTED TO SIGN,
DATE AND PROMPTLY RETURN THE ACCOMPANYING PROXY CARD IN THE ENCLOSED
POSTAGE-PAID ENVELOPE OR VOTE YOUR PROXY USING OUR TELEPHONE OR
INTERNET VOTING RESOURCES AS DESCRIBED ON THE PROXY CARD.

24
<PAGE>
REVOCABLE PROXY

THIS PROXY IS SOLICITED ON BEHALF OF THE BOARD OF DIRECTORS OF
ROSLYN BANCORP, INC.

ANNUAL MEETING OF STOCKHOLDERS
May 24, 2000
9:30 a.m., Eastern time

The undersigned hereby appoints the Board of Directors of Roslyn Bancorp,
Inc. (the "Company") to act as proxy for the undersigned, and to vote all shares
of Common Stock of the Company that the undersigned is entitled to vote at the
Annual Meeting of Stockholders, to be held on May 24, 2000, at 9:30 a.m.,
Eastern Time, at the Milleridge Cottage, 585 North Broadway, Jericho, New York,
and at any and all adjournments thereof, as indicated on the reverse side of
this proxy.

This proxy is revocable and will be voted as directed, but if no
instructions are specified, this proxy, properly signed and dated, will be voted
FOR each of the proposals listed. If any other business is presented at the
Annual Meeting, including whether or not to adjourn the meeting, this proxy will
be voted by the Board of Directors in their best judgment. At the present time,
the Board of Directors knows of no other business to be presented at the Annual
Meeting.

PLEASE COMPLETE, DATE, SIGN AND MAIL THIS PROXY PROMPTLY
IN THE ENCLOSED POSTAGE-PAID ENVELOPE OR
VOTE VIA THE INTERNET OR BY TELEPHONE.

(Continued, and to be marked, dated and signed, on the other side)

\/ FOLD AND DETACH HERE \/
- --------------------------------------------------------------------------------

ROSLYN BANCORP, INC. -- ANNUAL MEETING, MAY 24, 2000

YOUR VOTE IS IMPORTANT!

You can vote in one of three ways:

1. Call toll free 1-877-482-6155 on a Touch Tone telephone and follow the
instructions on the reverse side. There is NO CHARGE to you for this call.

2. Via the Internet at www.proxyvoting.com/Roslyn and follow the instructions.

or
--

3. Mark, sign and date your proxy card and return it promptly in the enclosed
envelope.

PLEASE VOTE

<PAGE>
The Board of Directors recommends a vote "FOR" each of the proposals presented.

<TABLE>
<S> <C>
1. The election as directors of all Please mark your votes as
nominees listed (except as marked indicated in this example [X]
to the contrary below):
2. The ratification of the appointment
With- For All of KPMG LLP as independent auditors of
For hold Except Roslyn Bancorp, Inc. for the fiscal
year ending December 31, 2000.
[_] [_] [_]
For [_] Against [_] Abstain [_]
Thomas J. Calabrese, Jr., Spiros J. Voutsinas
Leonard Genovese Dr. Edwin W. Martin, Jr.
Richard C. Webel 3. Such other matters as may properly
come before the meeting and at any
INSTRUCTION: To withhold authority to vote adjournments thereof, including
for any nominee(s), mark "For All Except" whether or not to adjourn the meeting.
and write that nominee(s') name(s) in the
space provided below.

</TABLE>

Please be sure to sign and date this Proxy in the box below.

Date ____________________

- --------------------------------- -----------------------------
Stockholder sign above Co-holder (if any) sign above

PLEASE CHECK BOX IF YOU PLAN TO ATTEND THE MEETING. [_]

The undersigned acknowledges receipt from the Company prior to the execution of
this proxy of a Notice of Annual Meeting of Stockholders, a Proxy Statement
dated April 17, 2000, and the Annual Report to Stockholders.

Please sign exactly as your name appears on this card. When signing as attorney,
executor, administrator, trustee or guardian, please give full title. If shares
are held jointly, each holder may sign, but only one signature is required.

* * * IF YOU WISH TO VOTE BY TELEPHONE OR INTERNET, PLEASE READ THE INSTRUCTIONS
BELOW * * *

FOLD AND DETACH HERE IF YOU ARE RETURNING YOUR PROXY CARD BY MAIL

VOTE BY TELEPHONE/INTERNET
QUICK * * * EASY * * * IMMEDIATE

Your telephone/Internet vote authorizes the named proxies to vote your shares in
the same manner as if you marked, signed and returned your proxy card.

Please have this card handy when you call. You'll need it in front of you in
order to complete the voting process.

VOTE BY PHONE: You will be asked to enter the Control Number (look below at
right).

<TABLE>
<S> <C>
OPTION A To vote as the Board of Directors recommends on ALL proposals,
press 1. Your vote will be confirmed.

OPTION B If you choose to vote on each proposal separately, press 0. You
will hear these instructions:

Item 1: To vote FOR ALL NOMINEES, press 1; to WITHHOLD FOR ALL
nominees, press 9.
To vote FOR ALL NOMINEES EXCEPT for certain of the
nominees, press 0 and listen to the instructions.

Item 2: To vote FOR, press 1; AGAINST, press 9;
ABSTAIN, press 0. When asked, you must confirm your
vote by pressing 1.

</TABLE>

VOTE BY INTERNET: The web address is www.proxyvoting.com/Roslyn

You will be asked to enter the Control Number (look below at right).

If you vote by telephone or Internet, DO NOT mail back your proxy. Proxies voted
by telephone or by Internet must be received by 12:00 a.m., Eastern time, on May
23, 2000.

THANK YOU FOR VOTING

<TABLE>
<S> <C>
Call * * * Toll Free * * * On a Touch Tone Telephone FOR TELEPHONE/
1-877-482-6155 - ANYTIME INTERNET VOTING:
There is NO CHARGE to you for this call. CONTROL NUMBER

</TABLE>

<PAGE>

REVOCABLE PROXY
ROSLYN BANCORP, INC.

[X] PLEASE MARK VOTES REVOCABLE PROXY
AS IN THIS EXAMPLE ROSLYN BANCORP, INC.
With- For All
For hold Except
ANNUAL MEETING OF STOCKHOLDERS E 1. The election as directors of all [__] [__] [__]
May 24, 2000 S nominees (except as marked to the
9:30 a.m., Eastern Time O contrary below):
This Proxy is Solicited on Behalf P
of the Board of Directors
Thomas J. Calabrese, Jr., Spiros J. Voutsinas, Leonard Genovese,
The undersigned hereby appoints the Board Dr. Edwin W. Martin, Jr. and Richard C. Webel
of Directors of Roslyn Bancorp, Inc.
(the "Company") to act as proxy for the INSTRUCTION: To withhold authority to vote for any individual nominee,
undersigned, and to vote all shares of mark "For All Except" and write that nominee's name in the space
Common Stock of the Company that the provided below.
undersigned is entitled to vote at the
Annual Meeting of Stockholders, to be _______________________________________________________________________
held on May 24, 2000, at 9:30 a.m.,
Eastern Time, at the Milleridge Cottage,
585 North Broadway, Jericho, New York, 2. The ratification of the appointment of KPMG For Against Abstain
and at any and all adjournments thereof, LLP as independent auditors of the Company [__] [__] [__]
as indicated on the reverse side of this for the fiscal year ending December 31, 2000.
proxy.
3. Such other matters as may properly come before the meeting and at
any adjournments thereof, including whether or not to adjourn the
meeting.

THE BOARD OF DIRECTORS RECOMMENDS A VOTE "FOR" EACH OF THE
PROPOSALS PRESENTED.

PLEASE CHECK BOX IF YOU PLAN TO ATTEND THE MEETING.

Please be sure to sign and date Date
this Proxy in the box below. ______________________

__________________________________________________________
Stockholder sign above Co-holder (if any) sign above

+----------------------------------------------------------------------------------------------------------------------------------+
Detach above card, sign, date and mail in postage paid envelop provided.

ROSLYN BANCORP, INC.
- ------------------------------------------------------------------------------------------------------------------------------------
IMPORTANT: The undersigned acknowledges receipt from the Company prior to the execution of this proxy of a Notice of Annual Meeting
of Stockholders, a Proxy Statement dated April 17, 2000, and the Annual Report to Stockholders.

Please sign exactly as your name appears on this card. When signing as attorney, executor, administrator, trustee or guardian,
please give your full title. If shares are held jointly, each holder may sign but only one signature is required.

PLEASE ACT PROMPTLY
SIGN, DATE & MAIL YOUR PROXY CARD TODAY
- ------------------------------------------------------------------------------------------------------------------------------------
</TABLE>

<PAGE>

REVOCABLE PROXY
ROSLYN BANCORP, INC.

<TABLE>
<S> <C> <C>
[X] PLEASE MARK VOTES REVOCABLE PROXY
AS IN THIS EXAMPLE ROSLYN BANCORP, INC.
With- For All
For hold Except
ANNUAL MEETING OF STOCKHOLDERS T 1. The election as directors of all [__] [__] [__]
May 24, 2000 R nominees (except as marked to the
9:30 a.m., Eastern Time E contrary below):
This Proxy is Solicited on Behalf S
of the Board of Directors O
P
Thomas J. Calabrese, Jr., Spiros J. Voutsinas, Leonard Genovese,
The undersigned hereby appoints the Board Dr. Edwin W. Martin, Jr. and Richard C. Webel
of Directors of Roslyn Bancorp, Inc.
(the "Company") to act as proxy for the INSTRUCTION: To withhold authority to vote for any individual nominee,
undersigned, and to vote all shares of mark "For All Except" and write that nominee's name in the space
Common Stock of the Company that the provided below.
undersigned is entitled to vote at the
Annual Meeting of Stockholders, to be _______________________________________________________________________
held on May 24, 2000, at 9:30 a.m.,
Eastern Time, at the Milleridge Cottage,
585 North Broadway, Jericho, New York, 2. The ratification of the appointment of KPMG For Against Abstain
and at any and all adjournments thereof, LLP as independent auditors of the Company [__] [__] [__]
as indicated on the reverse side of this for the fiscal year ending December 31, 2000.
proxy.
3. Such other matters as may properly come before the meeting and at
any adjournments thereof, including whether or not to adjourn the
meeting.

THE BOARD OF DIRECTORS RECOMMENDS A VOTE "FOR" EACH OF THE
PROPOSALS PRESENTED.

PLEASE CHECK BOX IF YOU PLAN TO ATTEND THE MEETING. [ ]
Please be sure to sign and date Date
this Proxy in the box below. ______________________

__________________________________________________________
Stockholder sign above Co-holder (if any) sign above

<PAGE>

<TABLE>
<S> <C> <C>
[X] PLEASE MARK VOTES REVOCABLE PROXY
AS IN THIS EXAMPLE ROSLYN BANCORP, INC.
With- For All
For hold Except
ANNUAL MEETING OF STOCKHOLDERS 4 1. The election as directors of all [__] [__] [__]
May 24, 2000 0 nominees (except as marked to the
9:30 a.m., Eastern Time 1 contrary below):
This Proxy is Solicited on Behalf (K)
of the Board of Directors
Thomas J. Calabrese, Jr., Spiros J. Voutsinas, Leonard Genovese,
The undersigned hereby appoints the Board Dr. Edwin W. Martin, Jr. and Richard C. Webel
of Directors of Roslyn Bancorp, Inc.
(the "Company") to act as proxy for the INSTRUCTION: To withhold authority to vote for any individual nominee,
undersigned, and to vote all shares of mark "For All Except" and write that nominee's name in the space
Common Stock of the Company that the provided below.
undersigned is entitled to vote at the
Annual Meeting of Stockholders, to be _______________________________________________________________________
held on May 24, 2000, at 9:30 a.m.,
Eastern Time, at the Milleridge Cottage,
585 North Broadway, Jericho, New York, 2. The ratification of the appointment of KPMG For Against Abstain
and at any and all adjournments thereof, LLP as independent auditors of the Company [__] [__] [__]
as indicated on the reverse side of this for the fiscal year ending December 31, 2000.
proxy.
3. Such other matters as may properly come before the meeting and at
any adjournments thereof, including whether or not to adjourn the
meeting.

THE BOARD OF DIRECTORS RECOMMENDS A VOTE "FOR" EACH OF THE
PROPOSALS PRESENTED.

Please be sure to sign and date Date
this Proxy in the box below. ______________________

__________________________________________________________
Stockholder sign above Co-holder (if any) sign above

[X] PLEASE MARK VOTES REVOCABLE PROXY
AS IN THIS EXAMPLE ROSLYN BANCORP, INC.
With- For All
For hold Except
ANNUAL MEETING OF STOCKHOLDERS I 1. The election as directors of all [__] [__] [__]
May 24, 2000 N nominees (except as marked to the
9:30 a.m., Eastern Time C contrary below):
This Proxy is Solicited on Behalf E
of the Board of Directors T Thomas J. Calabrese, Jr., Spiros J. Voutsinas, Leonard Genovese,
I Dr. Edwin W. Martin, Jr. and Richard C. Webel
The undersigned hereby appoints the Board V
of Directors of Roslyn Bancorp, Inc. E INSTRUCTION: To withhold authority to vote for any individual nominee,
(the "Company") to act as proxy for the mark "For All Except" and write that nominee's name in the space
undersigned, and to vote all shares of provided below.
Common Stock of the Company that the
undersigned is entitled to vote at the ---------------------------------------------------------------------
Annual Meeting of Stockholders, to be
held on May 24, 2000, at 9:30 a.m., 2. The ratification of the appointment of KPMG For Against Abstain
Eastern Time, at the Milleridge Cottage, LLP as independent auditors of the Company [__] [__] [__]
585 North Broadway, Jericho, New York, for the fiscal year ending December 31, 2000.
and at any and all adjournments thereof,
as indicated on the reverse side of this 3. Such other matters as may properly come before the meeting and at
proxy. any adjournments thereof, including whether or not to adjourn the
meeting.

THE BOARD OF DIRECTORS RECOMMENDS A VOTE "FOR" EACH OF THE
PROPOSALS PRESENTED.

PLEASE CHECK BOX IF YOU PLAN TO ATTEND THE MEETING. [__]

Please be sure to sign and date Date This proxy is revocable and will be voted as directed, but
this Proxy in the box below. _____________________ if no instructions are specified, this proxy, PROPERLY SIGNED
AND DATED, will be voted FOR each of the proposals listed
_________________________________________________________ above. If any other business is presented at the Annual
Stockholder sign above Co-holder (if any) sign above Meeting, this proxy will be voted by the Board of Directors
in their discretion. At the present time, the Board of
Directors knows of no other business to be presented at the
Annual Meeting.

+_____________________________________________________________________________________________________________________________+
/\ Detach above card, sign, date and mail in postage paid envelope provided. /\

ROSLYN BANCORP, INC.

____________________________________________________________________________________________________________________________________
IMPORTANT: The undersigned acknowledges receipt from the Company prior to the execution of this proxy of a Notice of Annual Meeting
of Stockholders, a Proxy Statement dated April 17, 2000, and the Annual Report to Stockholders.

PLEASE ACT PROMPTLY
SIGN, DATE & MAIL YOUR PROXY CARD TODAY
____________________________________________________________________________________________________________________________________
</TABLE>

<PAGE>

[Roslyn Letterhead]

Dear ESOP Participant:

In connection with the Annual Meeting of Stockholders of Roslyn Bancorp,
Inc. (the "Company"), the holding company for Roslyn Savings Bank (the "Bank"),
you may direct the voting of the shares of Company common stock held by the
Roslyn Savings Bank Employee Stock Ownership Plan ("ESOP") Trust allocated to
your account in the ESOP.

HSBC Bank USA has been appointed as trustee for the ESOP (the "ESOP
Trustee"). The ESOP Trustee will vote those shares of the Company's common
stock held in the ESOP Trust proportionally in accordance with instructions
given by the ESOP participants.

On behalf of the Board of Directors, I am forwarding to you a yellow proxy
card provided for the purpose of conveying your voting instructions to the ESOP
Trustee. Also enclosed is a Notice and Proxy Statement for the Company's Annual
Meeting of Stockholders and the Roslyn Bancorp, Inc. Annual Report to
Stockholders.

As of the Record Date, March 29, 2000, the ESOP Trust held 3,477,707 shares
of Common Stock, 392,783 shares of which have been allocated to participating
employees' accounts in the ESOP. These shares will be voted as directed by the
participants; provided timely instructions from the participants are received by
the ESOP Trustee. The unallocated shares in the ESOP Trust and the allocated
shares for which no instructions are provided, or for which no timely
instructions are received by the ESOP Trustee will be voted by the ESOP Trustee
in a manner calculated to most accurately reflect the instructions the ESOP
Trustee has received from participants regarding the shares of Common Stock
allocated to their accounts, so long as such vote is in accordance with the
Employee Retirement Income Security Act of 1974, as amended.

At this time, in order to direct the voting of the shares allocated to your
account under the ESOP, please fill out and sign the enclosed yellow proxy card
and return it in the enclosed postage-paid envelope no later than May 17, 2000.
Your vote will not be revealed, directly or indirectly, to any other officer or
other employee or director of the Company. The votes will be tallied and then
the ESOP Trustee will use the voting instructions it receives to vote the number
of shares in the ESOP Trust. As an employee of Roslyn Savings Bank you may
participate in several benefit plans. You will receive a proxy card for each of
these plans. Please vote all proxy cards received for each benefit plan in
which you are a participant.

Sincerely,

/s/ Joseph L. Mancino
Joseph L. Mancino
President, Vice Chairman of the Board
and Chief Executive Officer
<PAGE>

[Roslyn Letterhead]

Dear 401(k) Plan Participant:

In connection with the Annual Meeting of Stockholders of Roslyn Bancorp,
Inc. (the "Company"), the holding company for Roslyn Savings Bank, you may vote
the shares of Company common stock held in the Roslyn Savings Bank 401(k) Plan
Employer Stock Fund ("Employer Stock Fund") credited to your account in the
401(k) plan.

HSBC Bank USA has been appointed as trustee for the Employer Stock Fund.
The Employer Stock Fund Trustee will vote all shares for which no directions are
given, or for which timely instructions were not received in a manner calculated
to most accurately reflect the instructions the Employer Stock Fund Trustee
received from participants regarding shares in their Employer Stock Fund
accounts.

In order to provide the Employer Stock Fund Trustee with guidance in voting
the shares of the Company's common stock, you, as a participant investing in the
Employer Stock Fund, are being asked to provide voting instructions on the
enclosed green proxy card. Also enclosed is a Notice and Proxy Statement for
the Company's Annual Meeting of Stockholders and the Roslyn Bancorp, Inc. Annual
Report to Stockholders.

Please fill out and sign the enclosed green proxy card and return it in the
enclosed postage-paid envelope no later than May 17, 2000. Your vote will not
be revealed, directly or indirectly, to any other officer, other employee or
director of the Company. The votes will be tallied and the information provided
to the Employer Stock Fund Trustee who will vote the number of shares in the
Employer Stock Fund Trust. As an employee of Roslyn Savings Bank you may
participate in several benefit plans. You will receive a proxy card for each of
these plans. Please vote all proxy cards received for each benefit plan in
which you are a participant.

Sincerely,

/s/ Joseph L. Mancino
Joseph L. Mancino
President, Vice Chairman of the Board
and Chief Executive Officer
<PAGE>

[Roslyn Letterhead]

Dear Incentive Plan Participant:

In connection with the Annual Meeting of Stockholders of Roslyn Bancorp,
Inc. (the "Company"), the holding company for Roslyn Savings Bank (the "Bank"),
you may direct the voting of shares of Company common stock held in the Roslyn
Bancorp, Inc. 1997 Stock-Based Incentive Plan (the "Incentive Plan") Trust that
have been awarded to you. The Incentive Plan Trust holds _______________ shares
of Company common stock for the benefit of participants in the Incentive Plan.

On behalf of the Board of Directors, please find enclosed a blue proxy
card, provided for the purpose of conveying your voting instructions to First
Bankers Trust Company, NA (the "Incentive Plan Trustee"). Also enclosed is a
Notice and Proxy Statement for the Company's Annual Meeting of Stockholders and
the Roslyn Bancorp, Inc. Annual Report to Stockholders.

As of the Record Date, March 29, 2000, ____________ shares of Roslyn
Bancorp, Inc. common stock had been awarded to Incentive Plan participants. The
Incentive Plan Trustee will vote those shares of the Company's common stock held
in the Incentive Plan Trust in accordance with instructions of the participants.

At this time, in order to direct the voting of Company common stock granted
to you under the Incentive Plan, you must fill out and sign the enclosed blue
proxy card and return it in the enclosed postage-paid envelope no later than May
17, 2000. Your vote will not be revealed, directly or indirectly, to any
officer or other employee of the Company. The votes will be tallied and then
the Incentive Plan Trustee will use the voting instructions it receives to vote
the shares of Company common stock held in the Incentive Plan Trust. As an
employee of Roslyn Savings Bank you may participate in several benefit plans.
You will receive a proxy card for each of these plans. Please vote all proxy
cards received for each benefit plan in which you are a participant.

Sincerely,

/s/ Joseph L. Mancino
Joseph L. Mancino
President, Vice Chairman of the Board
and Chief Executive Officer
<PAGE>

[ROSLYN BANCORP LETTERHEAD]

Dear T R Financial Corp. ESOP Participant:

In connection with the Annual Meeting of Stockholders of Roslyn Bancorp,
Inc. (the "Company"), the holding company for Roslyn Savings Bank (the "Bank"),
you may direct the voting of shares of Company common stock held by the T R
Financial Corp. Employee Stock Ownership Plan (the "ESOP") Trust allocated to
your account in the ESOP as of March 29, 2000 (the "record date").

State Street Bank and Trust Company ("State Street" or the "Trustee"), an
unrelated corporate trustee, has been appointed as Trustee for the ESOP. The
Trustee will vote those shares of Company common stock held in the ESOP Trust
that have been allocated to participants' accounts in accordance with
instructions received from the participants. The unallocated shares held in the
ESOP will be voted proportionately to participants' voting instructions, so long
as such vote is in accordance with the requirements of the Employee Retirement
Income Security Act of 1974, as amended.

On behalf of the Board of Directors, I am forwarding to you a pink proxy
card provided for the purpose of conveying your voting instructions to the
Trustee. Also enclosed is a Notice and Proxy Statement for the Company's Annual
Meeting of Stockholders and the Roslyn Bancorp, Inc. Annual Report to
Stockholders.

As of March 29, 2000, the ESOP held_______________ shares of Company common
stock for the benefit of the participants of the ESOP. As a participant in the
ESOP, you may direct the voting of shares of Company common stock allocated to
your account in the ESOP. In order to direct the voting of the shares allocated
to your account, you must complete, sign and date the enclosed pink proxy card
and return it in the accompanying postage-paid envelope. Shares allocated to
your account will be voted as indicated on the enclosed pink proxy card. Your
proxy card must be received no later than May 17, 2000. Your vote will not be
revealed to the Company.

Your vote will be tallied and reported to the Trustee by Boston Equiserve
and then the Trustee will vote the number of shares in the ESOP for which it has
received voting instructions. The Trustee shall vote (a) any shares which have
been allocated to Participants' accounts for which no written instructions have
been received and (b) any unallocated shares in the ESOP in the same proportion
as shares for which instructions have been received. If you are an employee of
Roslyn Savings Bank you may participate in several benefit plans. You will
receive a proxy card for each of these plans. Please vote all proxy cards
received for each benefit plan in which you are a participant.

Sincerely,

/s/ Joseph L. Mancino
Joseph L. Mancino
President, Vice Chairman of the Board
and Chief Executive Officer