<PAGE>
<PAGE>

                                     Registration No. 333-______
As filed with the Securities and Exchange Commission on
                        December 30, 1999
================================================================
               SECURITIES AND EXCHANGE COMMISSION
                    Washington, D.C.  20549
          _______________________________________
                         FORM S-8
               REGISTRATION STATEMENT UNDER
                 THE SECURITIES ACT OF 1933
           _______________________________________


              CUMBERLAND MOUNTAIN BANCSHARES, INC.
    ______________________________________________________
    (Exact name of Registrant as Specified in Its Charter)

           TENNESSEE                           31-1499488
--------------------------------         ---------------------
(State or Other Jurisdiction             (I.R.S. Employer
of Incorporation or organization)        Identification No.)



                     1431 CUMBERLAND AVENUE
                   MIDDLESBORO, KENTUCKY 40965
                         (606) 248-4584
      --------------------------------------------------
           (Address of Principal Executive Offices)

CUMBERLAND MOUNTAIN BANCSHARES, INC. MANAGEMENT RECOGNITION PLAN
      CUMBERLAND MOUNTAIN BANCSHARES, INC. 1998 STOCK OPTION
                      AND INCENTIVE PLAN
----------------------------------------------------------------
                     (Full Title of the Plans)

                  JAMES J. SHOFFNER, PRESIDENT
              CUMBERLAND MOUNTAIN BANCSHARES, INC.
                    1431 CUMBERLAND AVENUE
                 MIDDLESBORO, KENTUCKY  40965
      -------------------------------------------------
             (Name and Address of Agent for Service)

                        (606) 248-4585
--------------------------------------------------------------
(Telephone Number, Including Area Code, of Agent for Service)

                      COPIES TO:
              GARY R. BRONSTEIN, ESQUIRE
               James C. Stewart, Esquire
              Joan S. Guilfoyle, Esquire
          Housley Kantarian & Bronstein, P.C.
           1220 19th Street N.W., Suite 700
                Washington, D.C.  20036
                    (202) 822-9611

<TABLE>
<CAPTION>

                        CALCULATION OF REGISTRATION FEE
=============================================================================
Title of Securities                        Proposed Maximum    Proposed Maximum      Amount Of
    To Be              Amount To Be         Offering Price    Aggregate Offering   Registration
 Registered           Registered (1)         Per Share (2)        Price (2)            Fee
-----------------------------------------------------------------------------------------------
<S>                      <C>                    <C>                  <C>                 <C>
 Common Stock,
 $.01 par value         61,562                 $(2)             $783,096            $207.00
================================================================================================
<FN>
(1)  Maximum number of shares issuable under the Cumberland Mountain Bancshares, Inc. Management
     Recognition Plan (17,589 shares) and the Cumberland Mountain Bancshares, Inc. 1998 Stock
     Option and Incentive Plan (43,973 shares), as such amounts may be increased in accordance
     with said plans in the event of a merger, consolidation, recapitalization, stock dividend,
     stock split or similar event involving the Registrant.
(2)  Under Rule 457(h) the registration fee may be calculated, inter alia, based upon the price
     at which the options may be exercised. Of the shares being registered hereby, 32,975 are
     under option at a weighted average exercise price of $16.00 per share ($527,600 in the
     aggregate).  The remainder of such shares, which are not presently subject to option (28,587
     shares), are being registered based upon the average of the bid and asked price of the
     common stock of the Registrant as reported on the OTC "Electronic Bulletin Board" on
     December 29, 1999 of $8.9375 per share ($255,496 in the aggregate).  Therefore, the
      total amount of the offering being registered herein is $783,096.

</FN>
</TABLE>

<PAGE>
<PAGE>
                        PART I

          INFORMATION REQUIRED IN THE SECTION
                   10(a) PROSPECTUS

ITEM 1.  PLAN INFORMATION*
------

Item 2.  REGISTRANT INFORMATION AND EMPLOYEE PLAN ANNUAL
------   INFORMATION*

       *Documents containing the information required by Part I
of this Registration Statement will be sent or given to
participants in the Cumberland Mountain Bancshares, Inc.
Management Recognition Plan and the Cumberland Mountain
Bancshares, Inc. 1998 Stock Option and Incentive Plan (together,
the "Plans") in accordance with Rule 428(b)(1).  In accordance
with Note to Part I of Form S-8, such documents are not filed
with the Securities and Exchange Commission (the "Commission")
either as part of this Registration Statement or as prospectuses
or prospectus supplements.


                         PART II

    INFORMATION REQUIRED IN THE REGISTRATION STATEMENT

ITEM 3.  INCORPORATION OF CERTAIN DOCUMENTS BY REFERENCE
------
       Cumberland Mountain Bancshares, Inc. (the "Company") is
subject to the informational requirements of the Securities
Exchange Act of 1934, as amended (the "1934 Act") and, accor-
dingly, files periodic reports and other information with the
Commission.  Reports, proxy statements and other information
concerning the Company filed with the Commission may be
inspected and copies may be obtained (at prescribed rates) at
the Commission's Public Reference Section, Room 1024, 450 Fifth
Street, N.W., Washington, D.C. 20549.  The Commission also main-
tains a Web site that contains reports, proxy and information
statements and other information regarding registrants that file
electronically with the Commission, including the Company.  The
address for the Commission's Web site is "http://www.sec.gov".

       The following documents are incorporated by reference in
this Registration Statement:

       (a)  The Company's Annual Report on Form 10-KSB for the
fiscal year ended June 30, 1999 (Commission File No. 0-22287).

       (b)  The Company's Quarterly Report on Form 10-QSB for
the quarter ended September 30, 1999 (Commission File No.
0-22287).

       (c)  The description of the Company's securities
contained in the Company's Form 8-A, as filed with the
Commission on March 25, 1997 (Commission File No. 0-22287).

       ALL DOCUMENTS FILED BY THE COMPANY PURSUANT TO SECTIONS
13(a), 13(c), 14, AND 15(d) OF THE SECURITIES EXCHANGE ACT OF
1934, AS AMENDED, PRIOR TO THE FILING OF A POST-EFFECTIVE
AMENDMENT WHICH INDICATES THAT ALL SECURITIES OFFERED HAVE BEEN
SOLD OR WHICH DEREGISTERS ALL SECURITIES THEN REMAINING UNSOLD,
SHALL BE DEEMED TO BE INCORPORATED BY REFERENCE IN THIS
REGISTRATION STATEMENT, AND TO BE A PART HEREOF FROM THE DATE OF
FILING OF SUCH DOCUMENTS.

ITEM 4.  DESCRIPTION OF SECURITIES
------
       Not applicable, as the Common Stock is registered under
Section 12 of the Securities Exchange Act of 1934.


ITEM 5.  INTERESTS OF NAMED EXPERTS AND COUNSEL
------
       Not Applicable.

                         1
<PAGE>
<PAGE>
ITEM 6.  INDEMNIFICATION OF DIRECTORS AND OFFICERS
------
       The directors and officers of the Company are entitled to
indemnification in certain circumstances.  Such indemnification
arises from Article XIII of the Company's Charter, separate
indemnification agreements entered into between the Company and
the Bank and the directors, and the Tennessee Business
Corporation Act.  In addition, the Bank currently maintains a
directors and officers liability policy to which the Company
will become party.  These provisions and contracts are described
briefly below.

ARTICLE XIII OF THE CHARTER

       Article XIII of the Company's Charter provides that
directors, officers, employees and agents may be indemnified in
certain circumstances against liability which they may incur in
their capacities.  Article XIII requires that the Company
indemnify any director who is made a party to any threatened,
pending, or completed action, suit or proceeding, whether civil,
criminal, administrative, or investigative ("proceeding"),
because he is or was a director against liability incurred in
such proceeding as long as he conducted himself in good faith,
he reasonably believed, (i) in the case of conduct in his
official capacity with the Company, that his conduct was in the
Company's best interests and (ii) in all other cases, that his
conduct was at least not opposed to its best interests; and, in
the case of any criminal proceeding, he had no reasonable cause
to believe his conduct was unlawful.  The Company must also
indemnify any director and any officer who is not a director if
he was wholly successful, on the merits or otherwise, in the
defense of any proceedings to which he was a party because he is
or was a director or officer of the Company against reasonable
expenses incurred by him in connection with the proceeding.
However, the Company may not indemnify a director in connection
with a proceeding by or in the right of the Company in which the
director was adjudged liable to the Company or in connection
with any other proceeding charging improper personal benefit to
him, whether or not involving action in his official capacity,
in which he was adjudged liable on the basis that personal
benefit was improperly received by him.

       Article XIII permits the Company to pay the reasonable
expenses incurred by a director who is a party to a proceeding
in advance of final disposition of the proceeding as long as:
(1) the director furnishes the Company a written affirmation of
his good faith belief that he has met the requisite standard of
conduct; (2) he provides the Company with a written undertaking
to repay such amounts if it is ultimately determined that he is
not entitled to indemnification; and (3) a determination is made
based on the facts then known, that indemnification is
permissible.

       The Company may not indemnify a director unless
authorized in the specific case after a determination has been
made that indemnification of the director is permissible in the
circumstances because he has met the required standards.  The
determination must be made: (1)  by the board of directors by
majority vote of a quorum consisting of directors not at the
time parties to the proceeding; (2) if a quorum cannot be
obtained, by majority vote of a committee duly designated by the
board of directors (in which designation directors who are
parties may participate), consisting solely of two or more
directors not at the time parties to the proceeding; (3) by
independent special legal counsel; or (4) by the shareholders,
but shares owned by or voted under the control of directors who
are at the time parties to the proceeding may not be voted on
the determination.

    The Company may indemnify and advance expenses to an
officer, employee or agent of the Company who is not a director
to the same extent as a director.

<PAGE>
INDEMNIFICATION AGREEMENTS

       The Company and the Bank have entered into written
indemnification agreements (the "Indemnification Agreements")
with each director of the Company and the Bank pursuant to which
the Company and the Bank will indemnify such individuals against
any and all expenses incurred by such individuals in connection
with any proceeding of any type to which such individual is made
or threatened to be made a party, as a result of or in connec-
tion with any action or inaction on the part of a director while
the director was or is a director or while the director was or
is serving at the request of the Company or the Bank as a
director, officer, employee or agent of another corporation,
partnership, joint venture, trust, employee benefit plan or
other enterprise.  Expenses covered by such agreements include,
without limitation, any judgment, amounts paid in settlement of
a proceeding, reasonable attorney's fees actually paid and
incurred in connection with a proceeding and reasonable
attorneys's fees, costs and expenses, if any, actually paid or
incurred in connection with a proceeding to enforce his rights
under the Indemnification Agreement.  The Indemnification
Agreements also provide for the prompt advancement of expenses
to the director in connection with investigating, defending or
being a witness in any proceeding.  The Indemnification


                              2
<PAGE>
<PAGE>
Agreements further provide a mechanism through which a director
may seek court relief in the event that the Company's or the
Bank's Board of Directors (or other person appointed by the
Board) determines that the directors would not be permitted to
be indemnified under applicable law.

       Notwithstanding the foregoing, no indemnification may be
made under the Indemnification Agreements for any of the
following:  (i) any act or omission for which the Bank is
prohibited to provide indemnification under federal law; (ii) to
the extent indemnification is prohibited by applicable regula-
tion or order properly issued by the FDIC or OTS under Section
18(k) of the Federal Deposit Insurance Act; (iii) to the extent
either the Bank or the Company has received a written objection
from the OTS to indemnification of the director, which written
objection is authorized by applicable law, regulation or order
relating specifically to indemnification, until such time as it
is permitted by the OTS; (iv) for any proceeding for which the
director is adjudged in a proceeding to be liable to the Bank or
the Company in the performance of his duty to the Bank, the
Company or their stockholders unless, and only to the extent
that, the court in which such proceeding is or was pending
determines that, in view of the circumstances, the director is
fairly and reasonably entitled to indemnity; (v) proceedings or
claims initiated or brought voluntarily by the director and not
by way of defense, except with respect to proceedings brought to
establish or enforce a right to indemnification under the
Indemnification Agreement or any other statute or law unless
otherwise determined by the Board of Directors; and (vi) any
amounts which have been paid directly to the director by an
insurance carrier under a policy of directors' liability
insurance maintained by the Bank or the Company.

TENNESSEE BUSINESS CORPORATION ACT

       The Tennessee Business Corporation Act requires Tennessee
corporations such as the Company to indemnify a director who was
wholly successful, on the merits or otherwise, in the defense of
any proceeding to which he was a party because he is or was a
directors of the corporation against reasonable expenses
incurred by him, unless the corporation's charter provides
otherwise.  The Tennessee Business Corporation Act also
generally permits Tennessee corporations to indemnify directors
and officers in the same manner as Article XIII of the Company's
Charter provides.  In no event, however, may a Tennessee
corporation indemnify a director if a judgment or other final
adjudication adverse to the director establishes his liability:
(i) for any breach of the duty of loyalty to the corporation or
its stockholders; (ii) for acts or omissions not in good faith
or which involve intentional misconduct or a knowing violation
of law; or (iii) for the approval of unlawful distributions.


DIRECTORS AND OFFICERS LIABILITY INSURANCE

       Pursuant to its Charter and Tennessee law, the Company is
permitted to purchase and maintain insurance on behalf of an
individual who is or was a director, officer, employee, or agent
of the Company.  The Bank currently maintains such a policy and
it is intended that the Company will become a party to such
policy.

ITEM 7.  EXEMPTION FROM REGISTRATION CLAIMED
------
       Not Applicable.

Item 8.  EXHIBITS
------

     The exhibits scheduled to be filed as part of this
Registration Statement are as follows:


   5.1  Opinion of Housley Kantarian & Bronstein, P.C.
        as to the validity of the Common Stock being
        registered

 23.1   Consent of Housley Kantarian & Bronstein, P.C.
        (appears in their opinion filed as Exhibit 5)

 23.2   Consent of Marr, Miller & Myers, PSC

 24     Power of Attorney (contained in the signature
        page to this registration statement)

 99.1   Cumberland Mountain Bancshares, Inc.
        Management Recognition Plan and associated
        Grantor Trust Agreement

 99.2   Cumberland Mountain Bancshares, Inc. 1998
        Stock Option and Incentive Plan

<PAGE>
<PAGE>
 99.3   1999 Amendment to the Cumberland Bancshares,
        Inc. 1998 Stock Option and Incentive Plan

 99.4   Form of Stock Option Agreement to be entered
        into with Optionees with respect to Incentive
        Stock Options granted under the Cumberland
        Mountain Bancshares, Inc. 1998 Stock Option
        and Incentive Plan

 99.5   Form of Stock Option Agreement to be entered
        into with Optionees with respect to
        Non-Incentive Stock Options granted under the
        Cumberland Mountain Bancshares, Inc. 1998
        Stock Option and Incentive Plan

 99.6   Form of Agreement to be entered into with
        Optionees with respect to Stock Appreciation
        Rights granted under the Cumberland Mountain
        Bancshares, Inc. 1998 Stock Option and
        Incentive Plan

 99.7   Notice of MRP Award

 99.8   Memorandum concerning taxation of MRP Awards,
        and associated election form


ITEM 9.  UNDERTAKINGS
------
       1.   The undersigned registrant hereby undertakes:

            (a)  To file, during any period in which it offers
or sells securities, a post-effective amendment to this
registration statement --

                 (i)  To include any prospectus required by
Section 10(a)(3) of the Securities Act of 1933;

                 (ii)  To reflect in the prospectus any facts or
events which, individually or together, represent a fundamental
change in the information in the registration statement.  Not-
withstanding the foregoing, any increase or decrease in volume
of securities offered (if the total dollar value of securities
offered would not exceed that which was registered) and any
deviation from the low or high end of the estimated maximum
offering range may be reflected in the form of prospectus filed
with the Commission pursuant to Rule 424(b) if, in the aggre-
gate, the changes in volume and price represent no more than a
20 percent change in the maximum aggregate offering price set
forth in the "Calculation of Registration Fee" table in the
effective registration statement.

                 (iii)  To include any additional or changed
material information on the plan of distribution.

provided, however, that paragraphs (a)(i) and (a)(ii) do not
apply if the registration statement is on Form S-3 or Form S-8,
and the information required to be included in a post-effective
amendment by those paragraphs is contained in periodic reports
filed by the registrant pursuant to Section 13 or 15(d) of the
Securities Exchange Act of 1934 that are incorporated by
reference in the registration statement.

            (b)  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 regis-
tration statement relating to the securities offered therein,
and the offering of the securities at that time shall be deemed
to be the initial bona fide offering thereof.

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

            (d) If the registrant is a foreign private issuer,
to file a post-effective amendment to the registration statement
to include any financial statements required by Rule 3-19 of
this chapter at the start of any delayed offering or throughout
a continuous offering.  Financial statements and information
otherwise required by Section 10(a)(3) of the Act need not be
furnished, provided, that the registrant includes in the
prospectus, by means of a post-effective amendment, financial
statements required pursuant to this paragraph  and other
information necessary to ensure that all other information in
the prospectus is at least as current as the date of those
financial statements.  Notwithstanding the foregoing, with
respect to registration statements on Form F-3, a post-effective
amendment need not be filed to include financial statements and
information required by Section 10(a)(3) of the Act or Rule 3-19
of this chapter if such financial statements and information are
contained in periodic reports filed with or furnished to the
Commission


                              4

<PAGE>
<PAGE>
by the registrant pursuant to Section 13 or Section 15(d) of the
Securities Exchange Act of 1934 that are incor-orated by
reference in the Form F-3.

       2.   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 15(d) of the Securities Exchange
Act of 1934 (and, where applicable, each filing of an employee
benefit plan's annual report pursuant to 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.

       3.   The undersigned registrant hereby undertakes to
deliver or cause to be delivered with the prospectus, to each
person to whom the prospectus is sent or given, the latest
annual report to security holders that is incorporated by
reference in the prospectus and furnished pursuant to and
meeting the requirements of Rule 14a-3 or Rule 14c-3 under the
Securities Exchange Act of 1934; and, where interim financial
information required to be presented by Article 3 of Regulation
S-X are not set forth in the prospectus, to deliver, or cause to
be delivered to each person to whom the prospectus is sent or
given, the latest quarterly report that is specifically incor-
porated by reference in the prospectus to provide such interim
financial information.

       4.   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 foregoing provisions, or otherwise, 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 indemni-
fication by it is against public policy as expressed in the Act
and will be governed by the final adjudication of such issue.


                             5

<PAGE>
<PAGE>

                        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 of 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 City of Middlesboro,
Commonwealth of Kentucky, on December 29, 1999.

                        CUMBERLAND MOUNTAIN BANCSHARES, INC.


                        By: /s/James J. Shoffner
                            --------------------------------
                            James J. Shoffner
                            President and Chief Managing Officer
                            (Duly Authorized Representative)


                     POWER OF ATTORNEY

    We, the undersigned Directors of Cumberland Mountain
Bancshares, Inc., hereby severally constitute and appoint J. Roy
Shoffner and James J. Shoffner, either of whom may act, with
full power of substitution, our true and lawful attorney and
agent, to do any and all things in our names in the capacities
indicated below which said J. Roy Shoffner and James J.
Shoffner, either of whom may act, may deem necessary or
advisable to enable Cumberland Mountain Bancshares, Inc. to
comply with the Securities Act of 1933, as amended, and any
rules, regulations and requirements of the Securities and
Exchange Commission, in connection with the registration of
Cumberland Mountain Bancshares, Inc. common stock, including
specifically, but not limited to, power and authority to sign
for us in our names in the capacities indicated below, the
registration statement and any and all amendments (including
post-effective amendments) thereto; and we hereby ratify and
confirm all that said J. Roy Shoffner and James J. Shoffner
shall do or cause to be done by virtue thereof.

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

<TABLE>
<CAPTION>

Signatures                           Title                                     Date
----------                           -----                                     ----
<S>                                   <C>                                      <C>
/s/J. Roy Shoffner            Chairman of the Board and                 December 29, 1999
-----------------------        Chief Executive Officer
 J. Roy Shoffner               (Principal Executive Officer)


 /s/James J. Shoffner          President and                            December 29, 1999
-----------------------        Chief Managing Officer;
 James J. Shoffner             Director


 /s/J. D. Howard               Senior Vice President;                   December 29, 1999
-----------------------        Chief Financial Officer; Corporate
 J. D. Howard                  Secretary and Treasurer (Principal
                               Financial and Accounting Officer)

 /s/Reccie Stagnolia, Jr.      Vice President; Branch                   December 29, 1999
-----------------------        Manager; Director
 Reccie Stagnolia, Jr.


 /s/Barry Litton               Director                                 December 29, 1999
-----------------------
 Barry Litton


 /s/Raymond C. Walker          Director                                 December 29, 1999
-----------------------
 Raymond C. Walker

</TABLE>
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{"company-data": {"conformed-name": "CUMBERLAND MOUNTAIN BANCSHARES INC", "cik": "0001029093", "assigned-sic": "6035", "irs-number": "311499488", "fiscal-year-end": "1231"}, "filing-values": {"form-type": "S-8", "act": "33", "file-number": "333-93909", "film-number": "99784080"}, "business-address": {"street1": "1431 CUMBERLAND AVE", "city": "MIDDLESBORO", "state": "KY", "zip": "40968"}, "mail-address": {"street1": "1431 CUMBERLAND AVE", "city": "MIDDLESBORO", "state": "KY", "zip": "40968"}}
Registration No. 333-______
As filed with the Securities and Exchange Commission on
                        December 30, 1999
================================================================
               SECURITIES AND EXCHANGE COMMISSION
                    Washington, D.C.  20549
          _______________________________________
                         FORM S-8
               REGISTRATION STATEMENT UNDER
                 THE SECURITIES ACT OF 1933
           _______________________________________

              CUMBERLAND MOUNTAIN BANCSHARES, INC.
    ______________________________________________________
    (Exact name of Registrant as Specified in Its Charter)

           TENNESSEE                           31-1499488
--------------------------------         ---------------------
(State or Other Jurisdiction             (I.R.S. Employer
of Incorporation or organization)        Identification No.)

                     1431 CUMBERLAND AVENUE
                   MIDDLESBORO, KENTUCKY 40965
                         (606) 248-4584
      --------------------------------------------------
           (Address of Principal Executive Offices)

CUMBERLAND MOUNTAIN BANCSHARES, INC. MANAGEMENT RECOGNITION PLAN
      CUMBERLAND MOUNTAIN BANCSHARES, INC. 1998 STOCK OPTION
                      AND INCENTIVE PLAN
----------------------------------------------------------------
                     (Full Title of the Plans)

                  JAMES J. SHOFFNER, PRESIDENT
              CUMBERLAND MOUNTAIN BANCSHARES, INC.
                    1431 CUMBERLAND AVENUE
                 MIDDLESBORO, KENTUCKY  40965
      -------------------------------------------------
             (Name and Address of Agent for Service)

                        (606) 248-4585
--------------------------------------------------------------
(Telephone Number, Including Area Code, of Agent for Service)

                      COPIES TO:
              GARY R. BRONSTEIN, ESQUIRE
               James C. Stewart, Esquire
              Joan S. Guilfoyle, Esquire
          Housley Kantarian & Bronstein, P.C.
           1220 19th Street N.W., Suite 700
                Washington, D.C.  20036
                    (202) 822-9611
CALCULATION OF REGISTRATION FEE
=============================================================================
Title of Securities                        Proposed Maximum    Proposed Maximum      Amount Of
    To Be              Amount To Be         Offering Price    Aggregate Offering   Registration
 Registered           Registered (1)         Per Share (2)        Price (2)            Fee
-----------------------------------------------------------------------------------------------
Common Stock,
 $.01 par value         61,562                 $(2)             $783,096            $207.00
================================================================================================
(1)  Maximum number of shares issuable under the Cumberland Mountain Bancshares, Inc. Management
     Recognition Plan (17,589 shares) and the Cumberland Mountain Bancshares, Inc. 1998 Stock
     Option and Incentive Plan (43,973 shares), as such amounts may be increased in accordance
     with said plans in the event of a merger, consolidation, recapitalization, stock dividend,
     stock split or similar event involving the Registrant.
(2)  Under Rule 457(h) the registration fee may be calculated, inter alia, based upon the price
     at which the options may be exercised. Of the shares being registered hereby, 32,975 are
     under option at a weighted average exercise price of $16.00 per share ($527,600 in the
     aggregate).  The remainder of such shares, which are not presently subject to option (28,587
     shares), are being registered based upon the average of the bid and asked price of the
     common stock of the Registrant as reported on the OTC "Electronic Bulletin Board" on
     December 29, 1999 of $8.9375 per share ($255,496 in the aggregate).  Therefore, the
      total amount of the offering being registered herein is $783,096.
PART I

          INFORMATION REQUIRED IN THE SECTION
                   10(a) PROSPECTUS

ITEM 1.  PLAN INFORMATION*
------

Item 2.  REGISTRANT INFORMATION AND EMPLOYEE PLAN ANNUAL
------   INFORMATION*

       *Documents containing the information required by Part I
of this Registration Statement will be sent or given to
participants in the Cumberland Mountain Bancshares, Inc.
Management Recognition Plan and the Cumberland Mountain
Bancshares, Inc. 1998 Stock Option and Incentive Plan (together,
the "Plans") in accordance with Rule 428(b)(1).  In accordance
with Note to Part I of Form S-8, such documents are not filed
with the Securities and Exchange Commission (the "Commission")
either as part of this Registration Statement or as prospectuses
or prospectus supplements.

                         PART II

    INFORMATION REQUIRED IN THE REGISTRATION STATEMENT

ITEM 3.  INCORPORATION OF CERTAIN DOCUMENTS BY REFERENCE
------
       Cumberland Mountain Bancshares, Inc. (the "Company") is
subject to the informational requirements of the Securities
Exchange Act of 1934, as amended (the "1934 Act") and, accor-
dingly, files periodic reports and other information with the
Commission.  Reports, proxy statements and other information
concerning the Company filed with the Commission may be
inspected and copies may be obtained (at prescribed rates) at
the Commission's Public Reference Section, Room 1024, 450 Fifth
Street, N.W., Washington, D.C. 20549.  The Commission also main-
tains a Web site that contains reports, proxy and information
statements and other information regarding registrants that file
electronically with the Commission, including the Company.  The
address for the Commission's Web site is "http://www.sec.gov".

       The following documents are incorporated by reference in
this Registration Statement:

       (a)  The Company's Annual Report on Form 10-KSB for the
fiscal year ended June 30, 1999 (Commission File No. 0-22287).

       (b)  The Company's Quarterly Report on Form 10-QSB for
the quarter ended September 30, 1999 (Commission File No.
0-22287).

       (c)  The description of the Company's securities
contained in the Company's Form 8-A, as filed with the
Commission on March 25, 1997 (Commission File No. 0-22287).

       ALL DOCUMENTS FILED BY THE COMPANY PURSUANT TO SECTIONS
13(a), 13(c), 14, AND 15(d) OF THE SECURITIES EXCHANGE ACT OF
1934, AS AMENDED, PRIOR TO THE FILING OF A POST-EFFECTIVE
AMENDMENT WHICH INDICATES THAT ALL SECURITIES OFFERED HAVE BEEN
SOLD OR WHICH DEREGISTERS ALL SECURITIES THEN REMAINING UNSOLD,
SHALL BE DEEMED TO BE INCORPORATED BY REFERENCE IN THIS
REGISTRATION STATEMENT, AND TO BE A PART HEREOF FROM THE DATE OF
FILING OF SUCH DOCUMENTS.

ITEM 4.  DESCRIPTION OF SECURITIES
------
       Not applicable, as the Common Stock is registered under
Section 12 of the Securities Exchange Act of 1934.

ITEM 5.  INTERESTS OF NAMED EXPERTS AND COUNSEL
------
       Not Applicable.

                         1
ITEM 6.  INDEMNIFICATION OF DIRECTORS AND OFFICERS
------
       The directors and officers of the Company are entitled to
indemnification in certain circumstances.  Such indemnification
arises from Article XIII of the Company's Charter, separate
indemnification agreements entered into between the Company and
the Bank and the directors, and the Tennessee Business
Corporation Act.  In addition, the Bank currently maintains a
directors and officers liability policy to which the Company
will become party.  These provisions and contracts are described
briefly below.

ARTICLE XIII OF THE CHARTER

       Article XIII of the Company's Charter provides that
directors, officers, employees and agents may be indemnified in
certain circumstances against liability which they may incur in
their capacities.  Article XIII requires that the Company
indemnify any director who is made a party to any threatened,
pending, or completed action, suit or proceeding, whether civil,
criminal, administrative, or investigative ("proceeding"),
because he is or was a director against liability incurred in
such proceeding as long as he conducted himself in good faith,
he reasonably believed, (i) in the case of conduct in his
official capacity with the Company, that his conduct was in the
Company's best interests and (ii) in all other cases, that his
conduct was at least not opposed to its best interests; and, in
the case of any criminal proceeding, he had no reasonable cause
to believe his conduct was unlawful.  The Company must also
indemnify any director and any officer who is not a director if
he was wholly successful, on the merits or otherwise, in the
defense of any proceedings to which he was a party because he is
or was a director or officer of the Company against reasonable
expenses incurred by him in connection with the proceeding.
However, the Company may not indemnify a director in connection
with a proceeding by or in the right of the Company in which the
director was adjudged liable to the Company or in connection
with any other proceeding charging improper personal benefit to
him, whether or not involving action in his official capacity,
in which he was adjudged liable on the basis that personal
benefit was improperly received by him.

       Article XIII permits the Company to pay the reasonable
expenses incurred by a director who is a party to a proceeding
in advance of final disposition of the proceeding as long as:
(1) the director furnishes the Company a written affirmation of
his good faith belief that he has met the requisite standard of
conduct; (2) he provides the Company with a written undertaking
to repay such amounts if it is ultimately determined that he is
not entitled to indemnification; and (3) a determination is made
based on the facts then known, that indemnification is
permissible.

       The Company may not indemnify a director unless
authorized in the specific case after a determination has been
made that indemnification of the director is permissible in the
circumstances because he has met the required standards.  The
determination must be made: (1)  by the board of directors by
majority vote of a quorum consisting of directors not at the
time parties to the proceeding; (2) if a quorum cannot be
obtained, by majority vote of a committee duly designated by the
board of directors (in which designation directors who are
parties may participate), consisting solely of two or more
directors not at the time parties to the proceeding; (3) by
independent special legal counsel; or (4) by the shareholders,
but shares owned by or voted under the control of directors who
are at the time parties to the proceeding may not be voted on
the determination.

    The Company may indemnify and advance expenses to an
officer, employee or agent of the Company who is not a director
to the same extent as a director.
INDEMNIFICATION AGREEMENTS

       The Company and the Bank have entered into written
indemnification agreements (the "Indemnification Agreements")
with each director of the Company and the Bank pursuant to which
the Company and the Bank will indemnify such individuals against
any and all expenses incurred by such individuals in connection
with any proceeding of any type to which such individual is made
or threatened to be made a party, as a result of or in connec-
tion with any action or inaction on the part of a director while
the director was or is a director or while the director was or
is serving at the request of the Company or the Bank as a
director, officer, employee or agent of another corporation,
partnership, joint venture, trust, employee benefit plan or
other enterprise.  Expenses covered by such agreements include,
without limitation, any judgment, amounts paid in settlement of
a proceeding, reasonable attorney's fees actually paid and
incurred in connection with a proceeding and reasonable
attorneys's fees, costs and expenses, if any, actually paid or
incurred in connection with a proceeding to enforce his rights
under the Indemnification Agreement.  The Indemnification
Agreements also provide for the prompt advancement of expenses
to the director in connection with investigating, defending or
being a witness in any proceeding.  The Indemnification

                              2
Agreements further provide a mechanism through which a director
may seek court relief in the event that the Company's or the
Bank's Board of Directors (or other person appointed by the
Board) determines that the directors would not be permitted to
be indemnified under applicable law.

       Notwithstanding the foregoing, no indemnification may be
made under the Indemnification Agreements for any of the
following:  (i) any act or omission for which the Bank is
prohibited to provide indemnification under federal law; (ii) to
the extent indemnification is prohibited by applicable regula-
tion or order properly issued by the FDIC or OTS under Section
18(k) of the Federal Deposit Insurance Act; (iii) to the extent
either the Bank or the Company has received a written objection
from the OTS to indemnification of the director, which written
objection is authorized by applicable law, regulation or order
relating specifically to indemnification, until such time as it
is permitted by the OTS; (iv) for any proceeding for which the
director is adjudged in a proceeding to be liable to the Bank or
the Company in the performance of his duty to the Bank, the
Company or their stockholders unless, and only to the extent
that, the court in which such proceeding is or was pending
determines that, in view of the circumstances, the director is
fairly and reasonably entitled to indemnity; (v) proceedings or
claims initiated or brought voluntarily by the director and not
by way of defense, except with respect to proceedings brought to
establish or enforce a right to indemnification under the
Indemnification Agreement or any other statute or law unless
otherwise determined by the Board of Directors; and (vi) any
amounts which have been paid directly to the director by an
insurance carrier under a policy of directors' liability
insurance maintained by the Bank or the Company.

TENNESSEE BUSINESS CORPORATION ACT

       The Tennessee Business Corporation Act requires Tennessee
corporations such as the Company to indemnify a director who was
wholly successful, on the merits or otherwise, in the defense of
any proceeding to which he was a party because he is or was a
directors of the corporation against reasonable expenses
incurred by him, unless the corporation's charter provides
otherwise.  The Tennessee Business Corporation Act also
generally permits Tennessee corporations to indemnify directors
and officers in the same manner as Article XIII of the Company's
Charter provides.  In no event, however, may a Tennessee
corporation indemnify a director if a judgment or other final
adjudication adverse to the director establishes his liability:
(i) for any breach of the duty of loyalty to the corporation or
its stockholders; (ii) for acts or omissions not in good faith
or which involve intentional misconduct or a knowing violation
of law; or (iii) for the approval of unlawful distributions.

DIRECTORS AND OFFICERS LIABILITY INSURANCE

       Pursuant to its Charter and Tennessee law, the Company is
permitted to purchase and maintain insurance on behalf of an
individual who is or was a director, officer, employee, or agent
of the Company.  The Bank currently maintains such a policy and
it is intended that the Company will become a party to such
policy.

ITEM 7.  EXEMPTION FROM REGISTRATION CLAIMED
------
       Not Applicable.

Item 8.  EXHIBITS
------

     The exhibits scheduled to be filed as part of this
Registration Statement are as follows:

   5.1  Opinion of Housley Kantarian & Bronstein, P.C.
        as to the validity of the Common Stock being
        registered

 23.1   Consent of Housley Kantarian & Bronstein, P.C.
        (appears in their opinion filed as Exhibit 5)

 23.2   Consent of Marr, Miller & Myers, PSC

 24     Power of Attorney (contained in the signature
        page to this registration statement)

 99.1   Cumberland Mountain Bancshares, Inc.
        Management Recognition Plan and associated
        Grantor Trust Agreement

 99.2   Cumberland Mountain Bancshares, Inc. 1998
        Stock Option and Incentive Plan
99.3   1999 Amendment to the Cumberland Bancshares,
        Inc. 1998 Stock Option and Incentive Plan

 99.4   Form of Stock Option Agreement to be entered
        into with Optionees with respect to Incentive
        Stock Options granted under the Cumberland
        Mountain Bancshares, Inc. 1998 Stock Option
        and Incentive Plan

 99.5   Form of Stock Option Agreement to be entered
        into with Optionees with respect to
        Non-Incentive Stock Options granted under the
        Cumberland Mountain Bancshares, Inc. 1998
        Stock Option and Incentive Plan

 99.6   Form of Agreement to be entered into with
        Optionees with respect to Stock Appreciation
        Rights granted under the Cumberland Mountain
        Bancshares, Inc. 1998 Stock Option and
        Incentive Plan

 99.7   Notice of MRP Award

 99.8   Memorandum concerning taxation of MRP Awards,
        and associated election form

ITEM 9.  UNDERTAKINGS
------
       1.   The undersigned registrant hereby undertakes:

            (a)  To file, during any period in which it offers
or sells securities, a post-effective amendment to this
registration statement --

                 (i)  To include any prospectus required by
Section 10(a)(3) of the Securities Act of 1933;

                 (ii)  To reflect in the prospectus any facts or
events which, individually or together, represent a fundamental
change in the information in the registration statement.  Not-
withstanding the foregoing, any increase or decrease in volume
of securities offered (if the total dollar value of securities
offered would not exceed that which was registered) and any
deviation from the low or high end of the estimated maximum
offering range may be reflected in the form of prospectus filed
with the Commission pursuant to Rule 424(b) if, in the aggre-
gate, the changes in volume and price represent no more than a
20 percent change in the maximum aggregate offering price set
forth in the "Calculation of Registration Fee" table in the
effective registration statement.

                 (iii)  To include any additional or changed
material information on the plan of distribution.

provided, however, that paragraphs (a)(i) and (a)(ii) do not
apply if the registration statement is on Form S-3 or Form S-8,
and the information required to be included in a post-effective
amendment by those paragraphs is contained in periodic reports
filed by the registrant pursuant to Section 13 or 15(d) of the
Securities Exchange Act of 1934 that are incorporated by
reference in the registration statement.

            (b)  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 regis-
tration statement relating to the securities offered therein,
and the offering of the securities at that time shall be deemed
to be the initial bona fide offering thereof.

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

            (d) If the registrant is a foreign private issuer,
to file a post-effective amendment to the registration statement
to include any financial statements required by Rule 3-19 of
this chapter at the start of any delayed offering or throughout
a continuous offering.  Financial statements and information
otherwise required by Section 10(a)(3) of the Act need not be
furnished, provided, that the registrant includes in the
prospectus, by means of a post-effective amendment, financial
statements required pursuant to this paragraph  and other
information necessary to ensure that all other information in
the prospectus is at least as current as the date of those
financial statements.  Notwithstanding the foregoing, with
respect to registration statements on Form F-3, a post-effective
amendment need not be filed to include financial statements and
information required by Section 10(a)(3) of the Act or Rule 3-19
of this chapter if such financial statements and information are
contained in periodic reports filed with or furnished to the
Commission

                              4
by the registrant pursuant to Section 13 or Section 15(d) of the
Securities Exchange Act of 1934 that are incor-orated by
reference in the Form F-3.

       2.   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 15(d) of the Securities Exchange
Act of 1934 (and, where applicable, each filing of an employee
benefit plan's annual report pursuant to 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.

       3.   The undersigned registrant hereby undertakes to
deliver or cause to be delivered with the prospectus, to each
person to whom the prospectus is sent or given, the latest
annual report to security holders that is incorporated by
reference in the prospectus and furnished pursuant to and
meeting the requirements of Rule 14a-3 or Rule 14c-3 under the
Securities Exchange Act of 1934; and, where interim financial
information required to be presented by Article 3 of Regulation
S-X are not set forth in the prospectus, to deliver, or cause to
be delivered to each person to whom the prospectus is sent or
given, the latest quarterly report that is specifically incor-
porated by reference in the prospectus to provide such interim
financial information.

       4.   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 foregoing provisions, or otherwise, 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 indemni-
fication by it is against public policy as expressed in the Act
and will be governed by the final adjudication of such issue.

                             5
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 of 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 City of Middlesboro,
Commonwealth of Kentucky, on December 29, 1999.

                        CUMBERLAND MOUNTAIN BANCSHARES, INC.

                        By: /s/James J. Shoffner
                            --------------------------------
                            James J. Shoffner
                            President and Chief Managing Officer
                            (Duly Authorized Representative)

                     POWER OF ATTORNEY

    We, the undersigned Directors of Cumberland Mountain
Bancshares, Inc., hereby severally constitute and appoint J. Roy
Shoffner and James J. Shoffner, either of whom may act, with
full power of substitution, our true and lawful attorney and
agent, to do any and all things in our names in the capacities
indicated below which said J. Roy Shoffner and James J.
Shoffner, either of whom may act, may deem necessary or
advisable to enable Cumberland Mountain Bancshares, Inc. to
comply with the Securities Act of 1933, as amended, and any
rules, regulations and requirements of the Securities and
Exchange Commission, in connection with the registration of
Cumberland Mountain Bancshares, Inc. common stock, including
specifically, but not limited to, power and authority to sign
for us in our names in the capacities indicated below, the
registration statement and any and all amendments (including
post-effective amendments) thereto; and we hereby ratify and
confirm all that said J. Roy Shoffner and James J. Shoffner
shall do or cause to be done by virtue thereof.

     Pursuant to the requirements of the Securities Act of 1933,
this Registration Statement has been signed by the following
persons in the capacities and on the dates indicated.
Signatures                           Title                                     Date
----------                           -----                                     ----
/s/J. Roy Shoffner            Chairman of the Board and                 December 29, 1999
-----------------------        Chief Executive Officer
 J. Roy Shoffner               (Principal Executive Officer)

 /s/James J. Shoffner          President and                            December 29, 1999
-----------------------        Chief Managing Officer;
 James J. Shoffner             Director

 /s/J. D. Howard               Senior Vice President;                   December 29, 1999
-----------------------        Chief Financial Officer; Corporate
 J. D. Howard                  Secretary and Treasurer (Principal
                               Financial and Accounting Officer)

 /s/Reccie Stagnolia, Jr.      Vice President; Branch                   December 29, 1999
-----------------------        Manager; Director
 Reccie Stagnolia, Jr.

 /s/Barry Litton               Director                                 December 29, 1999
-----------------------
 Barry Litton

 /s/Raymond C. Walker          Director                                 December 29, 1999
-----------------------
 Raymond C. Walker