LETTER TO CLIENTS

                           OFFER TO PURCHASE FOR CASH

                                       by

                     Crazy Woman Creek Bancorp Incorporated

        UP TO 350,000 SHARES OF ITS COMMON STOCK AT A PURCHASE PRICE NOT
               GREATER THAN $18.25 NOR LESS THAN $16.00 PER SHARE

THE OFFER AND WITHDRAWAL RIGHTS WILL EXPIRE AT 5:00 P.M. , MOUNTAIN TIME,
ON NOVEMBER 4, 2003, UNLESS THE OFFER IS EXTENDED.  CRAZY WOMAN CREEK
BANCORP INCORPORATED MAY EXTEND THE OFFER PERIOD AT ANY TIME.

                                                                 October 3, 2003

To Our Clients:

         Enclosed  for  your  consideration  are the  offer to  purchase,  dated
October 3, 2003, and the related  letter of  transmittal in connection  with the
offer by Crazy Woman  Creek  Bancorp  Incorporated,  a Wyoming  corporation,  to
purchase for cash 350,000 shares of its common stock, par value $0.10 per share,
at a price not greater  than  $18.25 nor less than $16.00 per share,  net to the
seller in cash, without interest,  as specified by shareholders  tendering their
shares.

         Given the prices specified by tendering  shareholders and the number of
shares  tendered  and  not  properly   withdrawn,   Crazy  Woman  Creek  Bancorp
Incorporated will select the lowest purchase price between $16.00 and $18.25 net
per share in cash,  without  interest,  that will allow it to  purchase  350,000
shares, or, if a lesser number of shares are properly tendered,  all shares that
are properly tendered. All shares acquired in the tender offer will be purchased
at the same price.

         Crazy Woman Creek Bancorp  Incorporated's  offer is being made upon the
terms and subject to the  conditions  set forth in its offer to purchase,  dated
October 3, 2003, and in the related letter of transmittal  which, as they may be
amended  and  supplemented  from time to time,  together  constitute  the tender
offer.

         Only shares properly  tendered at prices equal to or below the purchase
price and not properly  withdrawn  will be  purchased.  However,  because of the
proration  provisions  described  in the offer to  purchase,  all of the  shares
tendered  at or below  the  purchase  price  may not be  purchased  if more than
350,000  shares are properly  tendered.  All shares  tendered and not purchased,
including  shares  tendered at prices  above the  purchase  price and shares not
purchased  because of proration or the conditional  tender  procedures,  will be
returned  at  Crazy  Woman  Creek  Bancorp  Incorporated's  expense  as  soon as
practicable following the expiration date.

         Crazy Woman Creek Bancorp Incorporated  reserves the right, in its sole
discretion,  to purchase more than 350,000 shares pursuant to the offer, subject
to applicable  law.  Upon the terms and  conditions of Crazy Woman Creek Bancorp
Incorporated's  offer,  if more than  350,000  shares are  properly  tendered at
prices equal to or below the purchase  price and not properly  withdrawn,  Crazy
Woman Creek Bancorp  Incorporated  will purchase properly tendered shares in the
following order:

          o    First, all shares properly tendered and not properly withdrawn by
               any "odd lot holder" (as defined below) who:


                                     Page 1



               o    tenders all shares owned  (beneficially or of record) by the
                    odd lot  holder at a price  equal to or below  the  purchase
                    price  (tenders  of less than all the shares  owned will not
                    qualify for this  preference);  and

               o    completes  the section  entitled "Odd Lots" in the letter of
                    transmittal and, if applicable,  in the notice of guaranteed
                    delivery; and

          o    Second, after the purchase of all the shares properly tendered by
               odd lot holders and subject to the conditional  tender procedures
               described in section 5 of the offer to purchase, all other shares
               properly tendered at prices equal to or below the purchase price,
               on a  pro  rata  basis  with  appropriate  adjustments  to  avoid
               purchases of fractional shares.

         A TENDER OF YOUR  SHARES CAN BE MADE ONLY BY US AS THE HOLDER OF RECORD
AND PURSUANT TO YOUR INSTRUCTIONS. THE LETTER OF TRANSMITTAL IS FURNISHED TO YOU
FOR YOUR  INFORMATION  ONLY AND CANNOT BE USED BY YOU TO TENDER YOUR SHARES HELD
BY US FOR YOUR ACCOUNT.

         Accordingly,  please use the attached "Instruction Form" to instruct us
as to  whether  you wish us to tender  any or all of the shares we hold for your
account on the terms and subject to the conditions of the tender offer.

         WE CALL YOUR ATTENTION TO THE FOLLOWING:

          1.   You may tender  shares at prices not in excess of $18.25 nor less
               than $16.00 per share as indicated  in the  attached  Instruction
               Form, net to you in cash, without interest.

          2.   You should consult with your broker  regarding the possibility of
               designating  the  priority in which your shares will be purchased
               in the event of proration.

          3.   The tender offer is not  conditioned  upon any minimum  number of
               shares being tendered.  The tender offer is, however,  subject to
               certain other conditions described in the offer to purchase.

          4.   The tender offer and withdrawal  rights will expire at 5:00 p.m.,
               Mountain  time on Tuesday,  November 4, 2003,  unless Crazy Woman
               Creek Bancorp Incorporated extends the tender offer.

          5.   The   tender   offer   is  for   350,000   shares,   constituting
               approximately  43% of the  shares  outstanding  as of  October 3,
               2003.

          6.   Tendering  shareholders  who are registered  shareholders  or who
               tender their shares directly to Computershare  Trust Company Inc.
               as the  depositary,  will not be obligated  to pay any  brokerage
               commissions or fees,  solicitation  fees, or, except as set forth
               in the offer to  purchase  and the letter of  transmittal,  stock
               transfer  taxes  on  Crazy  Woman  Creek  Bancorp  Incorporated's
               purchase of shares under the tender offer.

          7.   If you are an odd lot holder,  meaning that you own  beneficially
               or of record  an  aggregate  of fewer  than 100  shares,  and you
               instruct  us to tender on your behalf all such shares at or below
               the purchase price before the  expiration  date and check the box
               captioned  "Odd Lots" in the  attached  instruction  form,  Crazy
               Woman Creek Bancorp Incorporated, upon the terms

                                     Page 2



               and subject to the  conditions of the tender  offer,  will accept
               all such shares for  purchase  before  proration,  if any, of the
               purchase  of other  shares  properly  tendered  at or  below  the
               purchase price and not properly withdrawn.

          8.   If you  wish to  tender  portions  of your  shares  at  different
               prices,  you must complete a separate  Instruction  Form for each
               price at which  you wish to  tender  each  such  portion  of your
               shares.  We must submit  separate  letters of transmittal on your
               behalf for each price you will accept.

          9.   The board of directors of Crazy Woman Creek Bancorp  Incorporated
               has approved the tender offer. However, neither Crazy Woman Creek
               Bancorp   Incorporated   nor  its  board  of  directors  nor  the
               information agent makes any  recommendation to shareholders as to
               whether  they should  tender or not tender  their shares or as to
               the price or prices at which  shareholders  may  choose to tender
               their  shares.  Shareholders  must make their own  decision as to
               whether to tender  their  shares  and,  if so, how many shares to
               tender  and the price or prices at which  such  shares  should be
               tendered.  Crazy Woman Creek Bancorp Incorporated's directors and
               executive   officers  have  advised  Crazy  Woman  Creek  Bancorp
               Incorporated  that they do not intend to tender any shares in the
               tender offer.

          10.  If you wish to have us tender any or all of your  shares,  please
               so instruct us by completing,  executing, detaching and returning
               to us the  attached  Instruction  Form.  If you  authorize  us to
               tender your  shares,  we will  tender all such shares  unless you
               specify otherwise on the attached Instruction Form.

         Please forward your Instruction Form to us as soon as possible to allow
us ample time to tender your shares on your behalf  prior to the  expiration  of
the offer.

         The tender  offer is being made solely  under the offer to purchase and
the related  letter of  transmittal  and is being made to all record  holders of
shares. The tender offer is not being made to, nor will tenders be accepted from
or on behalf of,  holders of shares  residing in any  jurisdiction  in which the
making of the tender offer or acceptance thereof would not be in compliance with
the securities, blue sky or other laws of such jurisdiction.

                                     Page 3



                                INSTRUCTION FORM

                      INSTRUCTIONS FOR TENDER OF SHARES OF
                     CRAZY WOMAN CREEK BANCORP INCORPORATED

         By signing this instruction form you acknowledge  receipt of our letter
and the  enclosed  offer to  purchase,  dated  October 3, 2003,  and the related
letter of transmittal in connection  with the offer by Crazy Woman Creek Bancorp
Incorporated,  a Wyoming  corporation,  to purchase  shares of its common stock,
$0.10 par value per share. Crazy Woman Creek Bancorp Incorporated is offering to
purchase up to 350,000  shares at a price not greater  than $18.25 nor less than
$16.00 per share, net to the seller in cash,  without interest,  as specified by
shareholders  tendering their shares.  Crazy Woman Creek Bancorp  Incorporated's
offer is being made upon the terms and  subject to the  conditions  set forth in
the offer to purchase and in the related letter of  transmittal,  which, as they
may be amended or supplemented from time to time, together constitute the offer.

         This  will   instruct  us  to  tender  to  Crazy  Woman  Creek  Bancorp
Incorporated,  on your behalf,  the number of shares  indicated  below (or if no
number is indicated below,  all shares) which are beneficially  owned by you but
registered  in our name,  upon the terms and  subject to the  conditions  of the
offer.

         Number of shares to be tendered:

          ___________________  shares.  (Unless otherwise indicated,  it will be
                                         assumed that all shares held by us  for
                                         your account are to be tendered.)

                        PRICE AT WHICH YOU ARE TENDERING
                (SEE INSTRUCTION 5 TO THE LETTER OF TRANSMITTAL)

You must check one box and only one box if you want to tender  your  shares.  If
more than one box is checked or if no box is  checked,  your  shares will not be
properly tendered.

SHARES TENDERED AT A PRICE DETERMINED BY YOU:

By checking one of the  following  boxes below  instead of the box under "Shares
tendered at a price determined  pursuant to the offer," you are tendering shares
at the price  checked.  This action  could  result in none of your shares  being
purchased  if  the  purchase   price  selected  by  Crazy  Woman  Creek  Bancorp
Incorporated for the shares is less than the price checked below. If you want to
tender  portions  of your  shares at more than one  price,  you must  complete a
separate  letter of transmittal  for each price at which you tender shares.  The
same shares cannot be tendered at more than one price.

PRICE (IN DOLLARS) PER SHARE AT WHICH SHARES ARE BEING TENDERED

[ ] $16.00             [ ] $16.75           [ ] $17.50
[ ] $16.25             [ ] $17.00           [ ] $17.75
[ ] $16.50             [ ] $17.25           [ ] $18.00
                                            [ ] $18.25

                                       OR

SHARES TENDERED AT A PRICE DETERMINED PURSUANT TO THE OFFER:

[ ]  By checking  this one box instead of one of the price boxes above,  you are
     tendering  shares and are willing to accept the purchase  price selected by
     Crazy Woman Creek Bancorp  Incorporated in accordance with the terms of the
     offer. This action will maximize the chance of having Crazy Woman

                                     Page 4



         Creek  Bancorp  Incorporated  purchase  your  shares  (subject  to  the
         possibility  of  proration).  Note  this  action  could  result in your
         receiving a price per share as low as $16.00.

                                    ODD LOTS
                (SEE INSTRUCTION 8 TO THE LETTER OF TRANSMITTAL)

Complete  this section  only if you own, or are  tendering on behalf of a person
who owns,  beneficially or of record,  an aggregate of fewer than 100 shares and
are tendering all of your shares.

You either (check one box):

[ ]  are the  beneficial  or  record  owner of an  aggregate  of fewer  than 100
     shares, all of which are being tendered; or

[ ]  are a broker, dealer, commercial bank, trust company, or other nominee that
     (a) is tendering for the beneficial owner(s),  shares with respect to which
     it is the record holder, and (b) believes,  based upon representations made
     to it by the beneficial  owner(s),  that each such person is the beneficial
     owner of an aggregate of fewer than 100 shares and is tendering  all of the
     shares.

                               CONDITIONAL TENDER
                (SEE INSTRUCTION 15 TO THE LETTER OF TRANSMITTAL)

You  may  condition   your  tender  of  shares  on  Crazy  Woman  Creek  Bancorp
Incorporated  purchasing a specified minimum number of your tendered shares, all
as described in section 5 of the offer to purchase. Unless the minimum number of
shares you indicate below is purchased by Crazy Woman Creek Bancorp Incorporated
in the offer,  none of the shares you  tendered  will be  purchased.  It is your
responsibility to calculate that minimum number of shares that must be purchased
if any are  purchased,  and you are urged to consult your own tax advisor before
completing  this section.  Unless this box has been checked and a minimum number
of shares specified, your tender will be deemed unconditional.

[ ]  The minimum number of shares that must be purchased,  if any are purchased,
     is: ____________ shares.

If because of proration,  the minimum number of shares that you designated above
will not be  purchased,  Crazy  Woman  Creek  Bancorp  Incorporated  may  accept
conditional  tenders by random lot, if  necessary.  However,  to be eligible for
purchase by random lot, you must have  tendered all your shares and checked this
box:

[ ]  The tendered shares represent all shares held by me.

         THE METHOD OF  DELIVERY  OF THIS  DOCUMENT IS AT THE OPTION AND RISK OF
THE TENDERING  SHAREHOLDER.  IF DELIVERY IS BY MAIL, REGISTERED MAIL WITH RETURN
RECEIPT REQUESTED,  PROPERLY INSURED, IS RECOMMENDED.  IN ALL CASES,  SUFFICIENT
TIME SHOULD BE ALLOWED TO ASSURE DELIVERY.

SIGN HERE:

Signature(s): __________________________________________________________________

Print Name(s): _________________________________________________________________

Address(es): ___________________________________________________________________

Area Code and Telephone Number: ________________________________________________

Taxpayer Identification or Social Security Number: _____________________________
Date: ______________________, 2003.

                                     Page 5