As filed with the Securities and Exchange Commission on October 25, 1999
Registration No. 333-

SECURITIES AND EXCHANGE COMMISSION
WASHINGTON, D.C. 20549

FORM S-8
REGISTRATION STATEMENT
Under
The Securities Act of 1933

FIRST OAK BROOK BANCSHARES, INC.
(Exact name of registrant as specified in its charter)

                 DELAWARE                     36-3220778
        (State of incorporation) (I.R.S. Employer Identification Number)


1400 SIXTEENTH STREET, OAK BROOK, ILLINOIS 60523
(Address of principal executive offices,
including zip code)

FIRST OAK BROOK BANCSHARES, INC.
DIRECTORS STOCK PLAN
(Full title of the Plan)

RICHARD M. RIESER, JR.
PRESIDENT
FIRST OAK BROOK BANCSHARES, INC.
1400 SIXTEENTH STREET
OAK BROOK, ILLINOIS 60523
(630) 571-1050
(Name, address, including zip code, and telephone
number, including area code, of agent for service)

Copies to:

  WILLIAM E. NAVOLIO, ESQ.                          THOMAS P. DESMOND, ESQ.
      GENERAL COUNSEL                         VEDDER, PRICE, KAUFMAN & KAMMHOLZ
FIRST OAK BROOK BANCSHARES, INC.            222 NORTH LASALLE STREET, SUITE 2600
   1400 SIXTEENTH STREET                          CHICAGO, ILLINOIS 60601-1003
 OAK BROOK, ILLINOIS 60523                               (312) 609-7647
     (630) 571-1050

CALCULATION OF REGISTRATION FEE

===================================================================================================================================
                                                             PROPOSED MAXIMUM        PROPOSED MAXIMUM
        TITLE OF SECURITIES             AMOUNT TO BE             OFFERING                AGGREGATE               AMOUNT OF
          TO BE REGISTERED              REGISTERED(1)       PRICE PER SHARE(2)       OFFERING PRICE(2)      REGISTRATION FEE(2)
--------------------------------------------------------- ----------------------- ----------------------- -----------------------
Common Stock $2 par value,               25,000 shs               $18.25                 $456,250                 $126.84
   including related preferred share
   purchase rights..................
========================================================= ======================= ======================= =======================

(1)  Together with an indeterminate number of additional shares which may be necessary to adjust the number of shares reserved for
     issuance pursuant to the Plan as a result of any future stock split, stock dividend or similar adjustment of the outstanding
     Common Stock or Class A Common Stock of the Company.
(2)  Estimated solely for the purpose of calculating the registration fee pursuant to Rule 457(h)(1) based upon the average of the
     high and low sales prices for the Common Stock reported on the Nasdaq National Market System as of October 19, 1999.
====================================================================================================================================


PART I

INFORMATION REQUIRED IN THE SECTION 10(a)
PROSPECTUS

This Registration Statement relates to the registration of 25,000 shares of Common Stock, $2 par value per share, including related preferred share purchase rights, of First Oak Brook Bancshares, Inc. (the "Registrant") reserved for issuance and delivery under the First Oak Brook Bancshares, Inc. Directors Stock Plan (the "Plan"). The documents containing the information required by this section will be given to directors participating in the Plan and are not required to be filed with the Commission as a part of the Registration Statement or as an Exhibit.

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PART II

INFORMATION REQUIRED IN THE REGISTRATION STATEMENT

ITEM 3. INCORPORATION OF DOCUMENTS BY REFERENCE.

The following documents of the Registrant filed or to be filed with the Commission are incorporated herein by reference:

(a) Registrant's Annual Report on Form 10-K for the year ended December 31, 1998.

(b) All other reports filed by Registrant pursuant to Section 13(a) or 15(d) of the Securities Exchange Act of 1934 since December 31, 1998.

(c) The description of the Common Stock, $2 par value, and the Class A Common Stock, $2 par value, and related preferred share purchase rights, of the Registrant contained in the Registrant's Registration Statement on Amendment No. 1 to Form 8-A filed with the Commission on or about May 6, 1999 pursuant to
Section 12 of the Securities Exchange Act of 1934, and the description of the preferred share purchase rights of the Registrant's Registration Statement on Form 8-A filed with the Commission on or about May 21, 1999, pursuant to Section 12 of the Securities Exchange Act of 1934, and all amendments and reports filed by the Registrant for the purpose of updating such descriptions.

In addition, each document or report subsequently filed by the Registrant with the Securities and Exchange Commission pursuant to Sections 13(a), 13(c), 14, and 15(d) of the Securities Exchange Act of 1934 after the date of this Registration Statement, but prior to the filing of a post-effective amendment to this Registration Statement which indicates that all securities offered by this Registration Statement have been sold or which deregisters all such securities then remaining unsold, shall be deemed to be incorporated by reference into this Registration Statement. Each document or report incorporated into this Registration Statement by reference shall be deemed to be a part of this Registration Statement from the date of the filing of such document with the Commission until the information contained therein is superseded or updated by any subsequently filed document which is incorporated by reference into this Registration Statement or by any subsequently filed amendment to this Registration Statement.

ITEM 4. DESCRIPTION OF SECURITIES

Not applicable.

ITEM 5. INTERESTS OF NAMED EXPERTS AND COUNSEL.

The validity of the shares of Common Stock and Class A Common Stock registered hereby is being passed upon for the Registrant by William E. Navolio, Vice President, General Counsel and Secretary of the Registrant. Mr. Navolio is the beneficial owner of less than 1% of the outstanding shares of Common Stock and Class A Common Stock, including shares which may be purchased pursuant to options granted under the Plan.

ITEM 6. INDEMNIFICATION OF DIRECTORS AND OFFICERS.

Section 145 of the Delaware General Corporation Law, as amended, grants the Registrant broad powers to indemnify any person in connection with legal proceedings brought against him by reason of his present or past status as an officer or director of the Registrant, provided that the person acted in good faith and in a manner he reasonably believed to be in or not opposed to the best interests of the Registrant, and with respect to any criminal action or proceeding, had no reasonable cause to believe this conduct was unlawful. This statute also gives the Registrant broad power to indemnify any such person against expenses in connection with any action by or in the right of the Registrant provided the person acted in good faith and in a manner he reasonably believed to be in or not opposed to the best interests of the Registrant except that no indemnification may be made if such person is adjudged to be liable to the Registrant unless and only to the extent the court in which such action was brought determines upon application that, despite such adjudication, but in view of all the circumstances of the case, the person is fairly and reasonably entitled

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to such indemnity as the court deems proper. In addition, to the extent that any such person is successful in the defense of any such legal proceeding, the Registrant is required by statute to indemnify him against expenses, including attorneys' fees, that are actually and reasonably incurred by him in connection therewith.

The effect of the foregoing provisions of the General Corporation Law of the State of Delaware and the Registrant's Amended and Restated By-laws would be to permit such indemnification by the Registrant for liabilities arising under the Securities Act of 1933.

ITEM 7. EXCEPTION FROM REGISTRATION CLAIMED.

Not applicable.

ITEM 8. EXHIBITS.

See Exhibit Index.

ITEM 9. UNDERTAKINGS.

(a) RULE 415 OFFERING.

The undersigned Registrant hereby undertakes:

(1) To file during any period in which offers or sales are being made, a post-effective amendment to this Registration Statement to include any material information with respect to the plan of distribution not previously disclosed in the Registration Statement or any material change to such information in the Registration Statement.

(2) That, for the purpose of determining any liability under the Securities Act of 1933, each such post-effective amendment shall be deemed to be a new registration statement relating to the securities offered therein, and the offering of such securities at that time shall be deemed to be the initial bona fide offering thereof.

(3) To remove from registration by means of a post-effective amendment any of the securities being registered that remain unsold at the termination of the offering.

(b) FILINGS INCORPORATING SUBSEQUENT EXCHANGE ACT DOCUMENTS BY REFERENCE.

The undersigned Registrant hereby undertakes that, for purposes of determining any liability under the Securities Act of 1933, each filing of the Registrant's annual report pursuant to Section 13(a) or Section 15(d) of the Securities Exchange Act of 1934 that is incorporated by reference in the Registration Statement shall be deemed to be a new registration statement relating to the securities offered therein, and the offering of such securities at that time shall be deemed to be the initial bona fide offering thereof.

(h) FILING OF REGISTRATION STATEMENT ON FORM S-8.

Insofar as indemnification for liabilities arising under the Securities Act of 1933 may be permitted to directors, officers and controlling persons of the Registrant pursuant to the provisions described in Item 6, the Registrant has been advised that in the opinion of the Securities and Exchange Commission such indemnification is against public policy as expressed in the Act and is, therefore, unenforceable. In the event that a claim for indemnification against such liabilities (other than the payment by the Registrant of expenses incurred or paid by a director, officer or controlling person of the Registrant in the successful defense of any action, suit or proceeding) is asserted by such director, officer or controlling person in connection with the securities being registered, the Registrant will, unless in the opinion of its counsel the matter has been settled by controlling precedent, submit to a court of appropriate jurisdiction the question whether such indemnification by it is against public policy as expressed in the Act and will be governed by the final adjudication of such issue.

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SIGNATURES

Pursuant to the requirements of the Securities Act of 1933, as amended, the Registrant certifies that it has reasonable grounds to believe that it meets all the requirements for filing on Form S-8 and has duly caused this Registration Statement to be signed on its behalf by the undersigned, thereunto duly authorized, in the Village of Oak Brook, State of Illinois on the 22nd day of October, 1999.

FIRST OAK BROOK BANCSHARES, INC.

By:  /s/ RICHARD M. RIESER, JR.
     --------------------------
     Richard M. Rieser, Jr., President

POWER OF ATTORNEY

KNOW ALL MEN BY THESE PRESENTS, that each person whose signature appears below constitutes and appoints Richard M. Rieser, Jr., William E. Navolio and Rosemarie Bouman, and each of them, as true and lawful attorney-in-fact and agent, with full power of substitution and resubstitution for him and in his/her name, place and stead, in any and all capacities, to sign any and all amendments (including post-effective amendments) to this Registration Statement, and to file the same, with all exhibits thereto, and other documents in connection therewith, with the Securities and Exchange Commission, granting unto said attorney-in-fact and agent full power and authority to do and perform each and every act and thing requisite and necessary to be done in and about the premises, as fully to all intents and purposes as he or she might or could do in person, hereby ratifying and confirming all that said attorney-in-fact and agent or his substitute may lawfully do or cause to be done by virtue hereof.

Pursuant to the requirements of the Securities Act of 1933, as amended, this Registration Statement has been signed by the following persons in the capacities and on the date indicated.

SIGNATURE                                                   TITLE                                DATE
---------                                                   -----                                ----

 /s/ EUGENE P. HEYTOW                        Chairman of the Board, Chief Executive        October 22, 1999
-----------------------------                        Officer and Director
Eugene P. Heytow

 /s/ RICHARD M. RIESER, JR.                          President and Director                October 22, 1999
-----------------------------
Richard M. Rieser, Jr.

 /s/ FRANK M. PARIS                              Vice Chairman of the Board and            October 22, 1999
-----------------------------                              Director
Frank M. Paris

 /s/ MIRIAM LUTWAK FITZGERALD                              Director                        October 22, 1999
-----------------------------
Miriam Lutwak Fitzgerald

 /s/ GEOFFREY R. STONE                                     Director                        October 22, 1999
-----------------------------
Geoffrey R. Stone

 /s/ ROBERT M. WROBEL                                      Director                        October 22, 1999
-----------------------------
Robert M. Wrobel

 /s/ MICHAEL L. STEIN                                      Director                        October 22, 1999
-----------------------------
Michael L. Stein

                                        4

SIGNATURE                                                   TITLE                                DATE
---------                                                   -----                                ----

 /s/ STUART I. GREENBAUM                                   Director                       October 22, 1999
-----------------------------
Stuart I. Greenbaum

 /s/ ROSEMARIE BOUMAN                         Vice President and Chief Financial          October 22, 1999
-----------------------------                  Officer (Principal Financial and
Rosemarie Bouman                                     Accounting Officer)

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                                  EXHIBIT INDEX

EXHIBIT
NUMBER              DESCRIPTION OF EXHIBIT
------              ----------------------
 4.1                First Oak Brook Bancshares, Inc. Directors Stock Plan
 5                  Opinion of William E. Navolio, Esq.
23.1                Consent of William E. Navolio, Esq. (included in Exhibit 5)
23.2                Consent of KPMG LLP
23.3                Consent of Ernst & Young LLP
24                  Power of Attorney (included on the signature pages of this
                    Registration Statement)


EXHIBIT 4.1

FIRST OAK BROOK BANCSHARES, INC.
DIRECTORS STOCK PLAN

1. Establishment; Purpose. First Oak Brook Bancshares, Inc. ("FOBB") establishes this First Oak Brook Bancshares, Inc. Directors Stock Plan (the "Stock Plan"), for the benefit of its directors, to be administered by the Chief Financial Officer of FOBB (the "Administrator"). The purpose of the Stock Plan is to provide an incentive to FOBB directors who are not employees of FOBB to remain as directors, increase their efforts for the success of FOBB, and encourage them to own additional shares of Common Stock of FOBB ("Common Stock"), thereby aligning their interests more closely with the interests of the stockholders of FOBB. This Stock Plan shall be effective July 1, 1999.

2. Election to Participate. Any director of FOBB who is not an employee of FOBB or any of its subsidiaries may elect to participate in the Stock Plan by filing an election with the Administrator. Elections to participate shall apply to a fiscal year commencing on July 1. Once an election has been filed with the Administrator, the director shall participate in the Stock Plan for the entire year in which he or she has initially elected to participate and for all subsequent years until the director files a notice of revocation of election with the Administrator. To be effective, any election or revocation under this paragraph 2 must be filed by the May 31st immediately preceding the July 1st on which it is to take effect.

3. Fees Paid in Stock. Commencing as of July 1 of the year a director elects to participate, all director fees earned by the director shall be paid in shares of Common Stock until the director shall cease to serve as a member of the FOBB board of directors or until June 30 of the year in which the director shall file a notice of revocation of election pursuant to paragraph 2, whichever first occurs. Director fees for this purpose shall be all fees paid to a director by reason of his or her being a member of any voting, non-advisory board of directors of FOBB or any committee thereof. The number of shares of Common Stock to be paid to a director shall be computed by dividing the total amount of fees earned by the director in a given period by the fair market value of one share of Common Stock as of the last business day on which trades in Common Stock were reported during the calendar quarter immediately preceding the quarter in which the period occurs. Fair market value as of any date means the closing price of the Common Stock on the NASDAQ National Market. Shares paid to a director shall be issued on a quarterly or more frequent basis as the Administrator shall determine.

4. Available Shares. Subject to paragraph 7 (relating to adjustments upon changes in capitalization), as of any date, the maximum number of shares of Common Stock issuable under the Stock Plan shall be 25,000.

5. Shares. Shares paid to directors under the Stock Plan shall be paid with newly issued shares of Common Stock of FOBB or treasury shares of Common Stock held by FOBB. No fractional shares shall be issued. Whenever the computation of the number of shares to be paid results in a fractional amount of one-half or greater, such amount shall be rounded up to the next greater whole number of shares and in all other cases such amount shall be rounded down to the next lower whole number of shares.

6. Securities Law Compliance. The Administrator may impose such requirements and restrictions with respect to any shares of Common Stock acquired under the Stock Plan as it may deem advisable including, without limitation, (a) legends and/or stop-transfer orders restricting transferability, and (b) investment and other representations from directors.

7. Adjustment in Capitalization. In the event that any change in the outstanding shares of Common Stock occurs by reason of a stock dividend, stock split, recapitalization, merger, consolidation, combination, share exchange or similar corporate change, the number of shares of Common Stock which may be issued under this Stock Plan shall be appropriately adjusted.

8. Deferred Stock Units. Directors who participate in the Stock Plan may elect to defer receipt of their shares of Common Stock otherwise payable under the Stock Plan and, in lieu thereof, FOBB shall maintain on its books deferred stock units ("Units") representing an obligation to issue shares of Common Stock. Units shall be credited to the director at the time and in the amount that shares of Common Stock would otherwise have been paid in the absence


of an election to defer. Additional Units shall be credited at the time dividends are paid on the Common Stock, as if such dividends were directors fees subject to this Stock Plan.

9. Nonassignment. Neither a director nor his or her duly designated beneficiary shall have any right to assign, transfer, pledge or otherwise convey the right to receive any Common Stock or Units hereunder, and any such attempted assignment, transfer, other conveyance shall not be recognized by FOBB.

10. Designation of Beneficiary. A director may designate the beneficiary which is to receive any unpaid Common Stock or Common Stock Payable with respect to Units credited at the director's death. Such designation shall be effective by filing a written notification with the Administrator and may be changed from time to time by similar action. If no such designation is made by a director, any such balance shall be paid to the director's estate.

11. Administrator. The Administrator shall establish the procedures and maintain all books and records in connection with the Stock Plan.

12. Amendment. The Plan may be amended or terminated at any time by action of the Board of Directors of FOBB, but no amendment shall adversely affect a director's rights with respect to fees earned but not yet paid in Common Stock or any Units without the director's written consent.


EXHIBIT 5

[LETTERHEAD OF WILLIAM E. NAVOLIO]

October 25, 1999

First Oak Brook Bancshares, Inc.
1400 Sixteenth Street
Oak Brook, Illinois 60523

Re: First Oak Brook Bancshares, Inc. Directors Stock Plan Legal Opinion Concerning the Validity of Shares Offered

Gentlemen:

I am Vice President, General Counsel and Secretary of First Oak Brook Bancshares, Inc., a Delaware corporation (the "Registrant" or "Company"), in connection with the registration under the Securities Act of 1933, as amended (the "Act"), of 25,000 shares of Common Stock, $2 par value per share and related preferred share purchase rights (collectively, the "Shares") of the Registrant. A registration statement on Form S-8 (the "Registration Statement") is being filed under the Act concurrently herewith to register the Shares which will be issued to eligible directors of the Registrant and participating subsidiaries pursuant to the above-referenced plan (the "Plan").

In connection with the offering of the Shares, I have examined:

(i) The Plan which is incorporated by reference as Exhibit 4.1 to the Registration Statement on Form S-8 of the Company;

(ii) the Registration Statement including the exhibits thereto; and

(iii)such other documents as I deemed necessary to form the opinions hereinafter expressed.

My opinion assumes that:

(a) The pertinent provisions of such blue sky and securities laws as may be applicable have been complied with; and

(b) The Shares are issued in accordance with the terms of the Plan.

Based and relying solely upon the foregoing, I advise you that, in my opinion, the Shares, or any portion thereof, to the extent such Shares represent original issuance by the Registrant, when issued pursuant to the Plan after the Registration Statement has become effective under the Act, will be validly issued, fully paid and non-assessable.

I hereby consent to the filing of this opinion as Exhibit 5 to the Registration Statement. In giving this consent, I do not thereby admit that I come within the category of persons whose consent is required under Section 7 of the Act or the rules and regulations of the Securities and Exchange Commission promulgated thereunder.

Very truly yours,

FIRST OAK BROOK BANCSHARES, INC.

/s/  WILLIAM E. NAVOLIO
--------------------------------
William E. Navolio
Vice President, General Counsel and Secretary


EXHIBIT 23.2

CONSENT OF INDEPENDENT AUDITORS

The Board of Directors
First Oak Brook Bancshares, Inc.:

We consent to the incorporation by reference in the Registration Statement on Form S-8 of First Oak Brook Bancshares, Inc. Directors Stock Plan of our report dated February 5, 1999, relating to the consolidated balance sheet of First Oak Brook Bancshares, Inc. and subsidiary as of December 31, 1998, and the related statements of income, changes in shareholders' equity and cash flows for the year ended December 31, 1998, which report appears in the December 31, 1998 annual report on Form 10-K of First Oak Brook Bancshares, Inc.

                                                  /s/  KPMG  LLP
                                                  ------------------------------

Chicago, Illinois
October 22, 1999


EXHIBIT 23.3

CONSENT OF INDEPENDENT AUDITORS

We consent to the incorporation by reference in the Registration Statement (Form S-8) pertaining to First Oak Brook Bancshares, Inc. Directors Stock Plan of our report dated January 20, 1998, with respect to the 1997 and 1996 consolidated financial statements of First Oak Brook Bancshares, Inc. incorporated by reference in its Annual Report (Form 10-K) for the year ended December 31, 1998, filed with the Securities and Exchange Commission.

                                             /s/  ERNST & YOUNG LLP
                                             -----------------------------------

Chicago, Illinois
October 20, 1999