UNITED STATES
                       SECURITIES AND EXCHANGE COMMISSION
                             WASHINGTON, D.C. 20549

                                   FORM 10-QSB



(Mark One)

 [X]    QUARTERLY  REPORT UNDER SECTION 13 OR 15(d) OF THE SECURITIES  EXCHANGE
        ACT OF 1934
                For the quarterly period ended December 31, 2000
                                               -----------------


 [ ]    TRANSITION  REPORT  UNDER  SECTION  13 OR  15(d)  OF THE ACT
                From the transition period from _____________ to

                Commission File Number 0-22287
                                       -------


                      CUMBERLAND MOUNTAIN BANCSHARES, INC.
        (Exact name of small business issuer as specified in its charter)

       Tennessee                                               31-1499488
(State of Incorporation)                       (IRS Employer Identification No.)

               1431 Cumberland Avenue, Middlesboro, Kentucky 40965
                    (Address of principal executive offices)

                                 (606) 248-4584
                               (Telephone number)

Check mark whether the issuer (1) has filed all reports  required to be filed by
Section 13 or 15(d) of the  Exchange  Act during the past 12 months (or for such
shorter period that the  registrant was required to file such reports),  and (2)
has been subject to such filing  requirements for the past 90 days.
Yes [X] No [  ]


                      APPLICABLE ONLY TO CORPORATE ISSUERS

As of January 31, 2001, there were 679,620 shares of common stock outstanding.

Transitional Small Business Disclosure Format (Check one):  Yes [  ]  No [X]




                      CUMBERLAND MOUNTAIN BANCSHARES, INC.
                         FORM 10-QSB - December 31, 2000

                                      INDEX


                                                                            Page
                                                                            ----
Part I - Financial Information
         ---------------------
     Item 1.      Financial Statements
         Consolidated Statement of Financial Condition
           December 31, 2000 and June 30, 2000                               2
         Consolidated Statements of Income
           Three and Six Months Ended December 31, 2000 and 1999           3-4
         Consolidated Statements of Stockholders' Equity
           Six Months Ended December 31, 2000                                5
         Consolidated Statements of Cash Flows
           Six Months Ended December 31, 2000 and 1999                     6-7
         Notes to the Consolidated Financial Statements                    8-9

     Item 2.      Management's Discussion and Analysis of Financial
                  Condition and Results of Operations                    10-16

Part II - Other Information                                                 17
          -----------------
Signatures                                                                  18






                      CUMBERLAND MOUNTAIN BANCSHARES, INC.
                              Middlesboro, Kentucky

                 CONSOLIDATED STATEMENTS OF FINANCIAL CONDITION
                             (Amounts in thousands)
                       December 31, 2000 and June 30, 2000

                                     ASSETS
                                     ------



                                                                                       December 31,    June 30,
                                                                                          2000          2000
                                                                                       -----------    --------

                                                                                              
Cash and cash equivalents                                                              $   5,038    $   1,581
Investment securities, held-to-maturity                                                     --           --
Investment securities available-for-sale, at market value                                  4,177        3,607
Other investments, held-to-maturity (market value $180,000 at
  December 30, 2000 and  June 30, 2000)                                                      180          180
Mortgage-backed securities available-for-sale, at market value                             1,904        2,626
Loans, net of allowance for loan losses of $1,010,000 at
  December 31, 2000 and $1,032,000 at June 30, 2000                                      105,804      109,610
Accrued interest receivable                                                                  858          809
Real estate held for investment                                                            1,558        1,669
Repossessed property                                                                       1,093        1,523
Federal Home Loan Bank (FHLB) stock, at cost                                                 964          929
Premises and equipment, net                                                                4,086        4,263
Prepaid expenses and other assets                                                          1,422        1,372
                                                                                       ---------    ---------
                                 TOTAL ASSETS                                          $ 127,084    $ 128,169
                                                                                       =========    =========

                      LIABILITIES AND STOCKHOLDERS' EQUITY
                      ------------------------------------

Deposits                                                                                 104,159      106,078
Advances from FHLB                                                                        10,500       10,500
Notes payable                                                                              2,978        1,485
Accrued interest payable                                                                      63          192
Other liabilities                                                                            932          799
                                                                                       ---------    ---------
          Total liabilities                                                              118,632      119,054
                                                                                       ---------    ---------
Common stock, $0.01 per value, 8,000,000 shares authorized, 679,620
  shares issued and outstanding                                                                7            7
Additional paid-in capital                                                                 5,549        5,560
Retained earnings                                                                          4,177        4,939
Unearned ESOP shares                                                                        (785)        (822)
Unearned Stock Option shares                                                                (329)        (329)
Unearned MRP shares                                                                          (90)         (90)
Net unrealized loss on investment securities available-for-sale, net of deferred tax         (77)        (150)
                                                                                       ---------    ---------
          Total stockholders' equity                                                       8,452        9,115
                                                                                       ---------    ---------

                  TOTAL LIABILITIES AND STOCKHOLDERS' EQUITY                           $ 127,084    $ 128,169
                                                                                       =========    =========


The accompanying notes are an integral part of these financial statements.



                                       2


                      CUMBERLAND MOUNTAIN BANCSHARES, INC.
                             Middlesboro, Kentucky

                        CONSOLIDATED STATEMENTS OF INCOME
              THREE AND SIX MONTHS ENDED DECEMBER 31, 2000 AND 1999
                  (Amounts in thousands, except per share data)


                                                                       Three Months          Six Months
                                                                    Ended December 31,     Ended December 31,
                                                                  -------------------------------------------
                                                                     2000       1999      2000        1999
                                                                     ----       ----      ----        ----
                                                                                        
INTEREST INCOME
      Investment securities                                        $    68    $    56    $   130    $   116
      Mortgage-backed securities                                        33         48         69         98
      Loans                                                          2,280      2,295      4,643      4,605
      FHLB Stock                                                        18         32         35         65
                                                                   -------    -------    -------    -------
           Total interest income                                     2,399      2,431      4,877      4,884

INTEREST EXPENSE
      Deposits                                                       1,329      1,264      2,670      2,519
      FHLB advances                                                    153        167        297        327
      Other borrowed money                                              38         35         74         71
                                                                   -------    -------    -------    -------
           Total interest expense                                    1,520      1,466      3,041      2,917

NET INTEREST INCOME                                                    879        965      1,836      1,967

PROVISION FOR LOAN LOSSES                                              225         98      1,003        160
                                                                   -------    -------    -------    -------
NET INTEREST INCOME AFTER PROVISION
  FOR LOAN LOSSES                                                      654        867        833      1,807
                                                                   -------    -------    -------    -------
NON-INTEREST INCOME
      Loan fees and service charges                                    169        204        355        405
      Gains (losses) on sales of investment securities                  --         (1)        --         (1)
      Gains (losses) on sales of repossessed assets                      6        (13)       (62)       (23)
      Gains (losses) on sales of real estate held for investment         9         (5)         9         11
      Other                                                             15          9         29         10
                                                                   -------    -------    -------    -------
           Total non-interest income                                   199        194        331        402
                                                                   -------    -------    -------    -------
NET INTEREST AND NON-INTEREST INCOME                                   853      1,061      1,164      2,209
                                                                   -------    -------    -------    -------
NON-INTEREST EXPENSE
      Salaries and employee benefits                                   384        374        783        747
      Data processing fees                                              60         60        120        114
      SAIF deposit insurance premiums                                   13         24         26         48
      Occupancy and equipment expense                                  136        144        275        290
      Franchise and other taxes                                         32         34         58         66
      Marketing and other professional services                         38         47         74         80
      ESOP expense                                                      13         13         26         26
      Other                                                            436        209        935        433
                                                                   -------    -------    -------    -------
           Total non-interest expense                                1,112        905      2,297      1,804
                                                                   -------    -------    -------    -------

INCOME BEFORE INCOME TAX EXPENSE                                      (259)       156     (1,133)       405

INCOME TAX EXPENSE                                                     (95)        48       (371)       131
                                                                   -------    -------    -------    -------
NET INCOME (LOSS)                                                  $  (164)   $   108    $  (762)   $   274
                                                                   -------    -------    -------    -------


                                       3


                      CUMBERLAND MOUNTAIN BANCSHARES, INC.
                             Middlesboro , Kentucky

                        CONSOLIDATED STATEMENTS OF INCOME
              THREE AND SIX MONTHS ENDED DECEMBER 31, 2000 AND 1999
                  (Amounts in thousands, except per share data)



                                                                       Three Months          Six Months
                                                                    Ended December 31,     Ended December 31,
                                                                   -------------------   --------------------
                                                                     2000       1999      2000        1999

                                                                                        

COMPREHENSIVE INCOME (LOSS)
      Net income (loss)                                            $   (164)   $   108    $   (762)  $   274
      Unrealized gain (loss) on securities, net of tax effect           (77)      (129)        (77)     (129)
                                                                   --------    -------    --------   -------
           OTHER COMPREHENSIVE INCOME (LOSS)                       $   (241)   $   (21)   $   (839)  $   145
                                                                   ========    =======    ========   =======
PER SHARE OF COMMON STOCK:
      Earnings (basic)                                             $(0.2917)   $0.1895    $(1.3552)  $0.4792
                                                                   ========    =======    ========   =======
      Earnings (diluted)                                           $(0.2625)   $0.1727    $(1.2221)  $0.4372
                                                                   ========    =======    ========   =======
      Dividends                                                    $   --      $  --      $   --     $   --
                                                                   ========    =======    ========   =======






The accompanying notes are an integral part of these financial statements.


                                       4

                      CUMBERLAND MOUNTAIN BANCSHARES, INC.
                              Middlesboro, Kentucky

                CONSOLIDTATED STATEMENTS OF STOCKHOLDERS' EQUITY
                             (Amounts in thousands)



                                                                                                                     Unrealized
                                                                                                                      Loss on
                                                                                                                     Investment
                                                                                     Additional                       Securities
                                                                       Common         Paid-In        Retained        Available-
                                                                        Stock         Capital        Earnings         for-Sale
                                                                       -------       ----------      --------        ----------

                                                                                                            
Balance at June 30, 2000                                                 $ 7          $ 5,560         $4,939            $ (150)

Net income for the six month period ended
  December 31, 2000                                                        -                -           (762)                -

Common stock issued                                                        -                -              -                 -

ESOP shares transferred                                                    -                -              -                 -

ESOP shares earned                                                         -              (11)             -                 -

Stock Option shares transferred                                            -                -              -                 -

MRP shares acquired                                                        -                -              -                 -

Decrease in unrealized loss on investment
  securities available-for-sale for the period
  ended December 31, 2000, net of deferred tax                             -                -              -                73
                                                                         ---          -------         ------             -----
Balance at December 31, 2000                                             $ 7          $ 5,549         $4,177             $ (77)
                                                                         ===          =======         ======             =====


                                                                              Unearned
                                                              Unearned          Stock          Unearned
                                                               ESOP             Option           MRP           Treasury
                                                               Shares           Shares          Shares          Stock        Total
                                                               -------        ---------         -------        --------      -----

                                                                                                            
Balance at June 30, 2000                                       $ (822)          $ (329)          $ (90)            $ -     $ 9,115

Net income for the six month period ended
  December 31, 2000                                                 -                -               -               -        (762)

Common stock issued                                                 -                -               -               -           -

ESOP shares transferred                                             -                -               -               -           -

ESOP shares earned                                                 37                -               -               -          26

Stock Option shares transferred                                     -                -               -               -           -

MRP shares acquired                                                 -                -               -               -           -

Decrease in unrealized loss on investment
  securities available-for-sale for the period
  ended December 31, 2000, net of deferred tax                      -                -               -               -          73
                                                               ------           ------           -----             ---     -------
Balance at December 31, 2000                                   $ (785)          $ (329)          $ (90)            $ -     $ 8,452
                                                               ======           ======           =====             ===     =======




The accompanying notes are an integral part of these financial statements.


                                       5


                      CUMBERLAND MOUNTAIN BANCSHARES, INC.
                              Middlesboro, Kentucky

                      CONSOLIDATED STATEMENTS OF CASH FLOWS
                             (Amounts in thousands)
                          Six Months Ended December 31,



                                                                                                2000              1999
                                                                                              -------           --------
                                                                                                           
CASH FLOWS FROM OPERATING ACTIVITIES
     Net income                                                                               $ (762)          $   274
     Adjustments to reconcile net income to net cash provided by (used in)
       operating activities
        Depreciation                                                                             216               203
        Amortization and accretion                                                                 5                 6
        FHLB stock dividend                                                                      (35)              (66)
        Provision for loan losses                                                              1,003               160
        (Gains) losses on sales of investment securities                                          --                 1
        (Gains) losses on sales of other repossessed assets                                       62                23
        (Gains) losses on sales of property held for investment                                   (9)              (11)
        Changes in assets and liabilities:
           Accrued interest receivable                                                           (49)              125
           Prepaid expenses and other assets                                                     (50)           (1,280)
           Accrued interest payable                                                             (129)               24
           Other liabilities                                                                     133               513
                                                                                              ------           -------
               Net cash provided by (used in) operating activities                               385               (28)
                                                                                              ------           -------

CASH FLOWS FROM INVESTING ACTIVITIES
     Purchase of investment securities available-for-sale                                       (500)           (1,000)
     Proceeds on maturities of investment securities available-for-sale                           --               500
     Principal collected on investment securities available-for-sale                              13               140
     Proceeds on sales of other investments                                                       --                15
     Proceeds on maturities of mortgage-backed securities                                        391                --
     Principal collected on mortgage-backed securities                                           357               471
     Net (increase) decrease in real estate held for investment                                  120              (300)
     Net (increase) decrease in loans                                                          2,760             1,719
     Net (increase) decrease in repossessed property                                             368              (352)
     Purchases of premises and equipment                                                         (39)              (55)
                                                                                              ------           -------
               Net cash provided by (used in) investing activities                             3,470             1,138
                                                                                              ------           -------

CASH FLOWS FROM FINANCING ACTIVITIES
     Net increase (decrease) in deposits                                                      (1,919)            1,690
     Net increase (decrease) in advances from FHLB                                                --               500
     Net increase (decrease) in other borrowings                                               1,493               (59)
     ESOP shares earned, net of tax                                                               28                38
     Purchase of shares for MRP                                                                   --              (103)
                                                                                              ------           -------
               Net cash provided by (used in) financing activities                              (398)            2,066



The accompanying notes are an integral part of these financial statements.


                                       6


                      CUMBERLAND MOUNTAIN BANCSHARES, INC.
                              Middlesboro, Kentucky

                      CONSOLIDATED STATEMENTS OF CASH FLOWS
                             (Amounts in thousands)
                          Six Months Ended December 31,



                                                                                               2000              1999
                                                                                             -------           --------
                                                                                                         
NET INCREASE (DECREASE) IN CASH AND CASH EQUIVALENTS                                           3,457             3,176

CASH AND CASH EQUIVALENTS, BEGINNING OF PERIOD                                                 1,581             1,317
                                                                                             -------           -------
CASH AND CASH EQUIVALENTS, END OF PERIOD                                                     $ 5,038           $ 4,493
                                                                                             =======           =======
SUPPLEMENTAL DISCLOSURES
     Cash paid for:
           Interest                                                                          $ 1,650           $   631
                                                                                             =======           =======
           Income taxes                                                                      $    --           $    --
                                                                                             =======           =======
     Loans transferred to repossessed property during the period                             $    93           $   322
                                                                                             =======           =======
     Total increase (decrease) in unrealized gain (loss) on
       securities available for sale                                                         $    73           $     9
                                                                                             =======           =======



The accompanying notes are an integral part of these financial statements.


                                       7

                      CUMBERLAND MOUNTAIN BANCSHARES, INC.
                              Middlesboro, Kentucky

                 NOTES TO THE CONSOLIDATED FINANCIAL STATEMENTS
                               December 31, 2000
                                   (UNAUDITED)


NOTE 1 -      BASIS OF PRESENTATION

     The accompanying  unaudited consolidated financial statements were prepared
in accordance with instructions for Form 10-QSB and,  therefore,  do not include
all  information  and notes  necessary for a complete  presentation of financial
position, results of operations, changes in stockholders' equity, and cash flows
in conformity  with  generally  accepted  accounting  principles.  However,  all
adjustments (consisting only of normal recurring accruals) which, in the opinion
of  management,   are  necessary  for  a  fair  presentation  of  the  unaudited
consolidated   financial  statements  have  been  included  in  the  results  of
operations for the six months ended December 31, 2000 and 1999.

     Operating  results for the six month period ended  December 31, 2000 is not
necessarily  indicative  of the results that may be expected for the year ending
June 30, 2001.

     Prior to March 31, 1997,  the  Cumberland  Mountain  Bancshares,  Inc. (the
"Company") did not have any material assets or liabilities and did not engage in
any material business operations. On March 31, 1997, the Company acquired all of
the  outstanding  stock of Middlesboro  Federal Bank,  Federal Savings Bank (the
"Bank")  pursuant to the Plan of Conversion of Cumberland  Mountain  Bancshares,
M.H.C., the Bank's former mutual holding company,  and the Agreement and Plan of
Reorganization  between  the  Company  and the  Bank.  In  connection  with  the
Conversion and  Reorganization,  the Company sold 439,731 shares of Common Stock
in an  initial  public  offering  and  issued  1.333  shares of Common  Stock in
exchange  for each  share of the  Bank's  common  stock  then  outstanding.  The
Company's  financial  statements for the periods prior to March 31, 1997 consist
of the financial statements of the Bank.

NOTE 2 -      ALLOWANCE FOR LOAN LOSSES

     Activity in the allowance for loan losses is summarized as follows (amounts
in thousands):

                                                                  December 31,
                                                                      2000
                                                                  ------------
                  Balance, beginning of year                       $ 1,032
                  Provision for loan losses                          1,003
                  Charge-offs, net of recoveries                    (1,025)
                                                                   -------
                  Balance, December 31, 2000                       $ 1,010
                                                                   =======


                                       8


                      CUMBERLAND MOUNTAIN BANCSHARES, INC.
                              Middlesboro, Kentucky

                 NOTES TO THE CONSOLIDATED FINANCIAL STATEMENTS
                               December 31, 2000
                                   (UNAUDITED)


NOTE 3 -      NONACCRUAL LOANS

         Nonaccrual loans are as follows (amounts in thousands):



                                                                       December 31,      June 30,
                                                                           2000            2000
                                                                       -----------       --------

                                                                                    
                  Construction Mortgage Loans                          $  --              $ --
                  Permanent Mortgage Loans, Secured by:
                     1-4 Dwelling Units                                  202               493
                     5 or More Dwelling Units                             --                --
                     Nonresidential Property (Except Land)               275                73
                     Land                                                 47                --
                  Nonmortgage Loans and Leases, Closed End:
                     Commercial                                           55               194
                     Auto                                                 20                14
                     Mobile Home                                          --                --
                     Other Consumer                                       16                17
                  Nonmortgage Loans and Leases, Open End:
                     Revolving Loans Secured by
                       1-4 Dwelling Units                                 --                --
                                                                       -----              ----
                                                                       $ 615              $791
                                                                       =====              ====



                                       9


                      CUMBERLAND MOUNTAIN BANCSHARES, INC.
                              Middlesboro, Kentucky

                      MANAGEMENT'S DISCUSSION AND ANALYSIS



GENERAL

     The  principal  business  of  Cumberland  Mountain  Bancshares,  Inc.  (the
"Company")  is that of  Middlesboro  Federal Bank,  FSB (the  "Savings  Bank" or
"Middlesboro  Federal").  The principal business of the Savings Bank consists of
accepting  deposits from the general  public and investing  these funds in loans
secured by  one-to-four  family  owner-occupied  residential  properties  in the
Savings  Bank's  primary  market  area.  The  Savings  Bank  also  maintains  an
investment  portfolio  which  includes  Federal Home Loan Bank  ("FHLB")  stock,
Government  Agency-issued  bonds  and  mortgage-backed   securities,  and  other
investments.

FORWARD-LOOKING STATEMENTS

     In addition to  historical  information  contained  herein,  the  following
discussion   contains   forward-looking   statements   that  involve  risks  and
uncertainties.   Economic  circumstances,   the  Company's  operations  and  the
Company's actual results could differ  significantly from those discussed in the
forward-looking  statements.  Some of the factors that could cause or contribute
to such differences are discussed herein but also include changes in the economy
and interest rates in the nation and the Company's  market area generally.  Some
of the forward-looking  statements included herein are the statements  regarding
management's  determination of the amount and adequacy of the allowance for loan
losses on loans, the effect of certain recent accounting pronouncements.

FINANCIAL CONDITION

     Total assets of the Company have decreased 0.85% from  $128,169,000 at June
30, 2000 to  $127,084,000  at December  31,  2000.  This  decrease in assets has
resulted  primarily from the decrease in net loans of $3.8 million,  or 3.47% to
$105,804,000  at  December  31, 2000 from  $109,610,000  at June 30,  2000.  The
decline in net loans is primarily  due to lower loan volume and net  charge-offs
of $1,025,000  during the six-month period ended December 31, 2000. This decline
in loans was  partially  offset by an increase in cash and cash  equivalents  of
$3.5 million.

     During the six months ended December 31, 2000, the Savings Bank  recognized
charge-offs on several large commercial borrowers. These charge-offs resulted in
a severe  reduction in the Savings Bank's  allowance for loan losses for the six
months ended December 31, 2000.  Pursuant to  recommendations  by the Classified
Assets  Committee of the Savings Bank, a provision for loan losses of $1,003,000
was made during the six months ended December 31, 2000. The Committee determined
this was the amount needed to  adequately  provide for future  potential  losses
based upon the level of classified assets.

     The Company  has  experienced  a decline in deposits  during the six months
ended December 31, 2000 of $1,919,000,  or 1.81%.  This decline is primarily the
result of higher interest rates and increased  competition in the Savings Bank's
market area for deposits.  Notes Payable increased $1,493,000 from $1,485,000 at
June 30, 2000 to $2,978,000  at December 31, 2000.  This increase was due to the
refinancing  of an  intra-company  debt with an  outside  creditor.  During  the
quarter  ended  December 31,  2000,  the Company  borrowed  $1.6 million from an
outside lender which was contributed to the Company's subsidiary,  Home Mortgage
Loan Corporation  ("HMLC").  HMLC used such funds to repay an intercompany loan.
The loan from the outside lender is secured by all of the issued and outstanding
shares of the Savings Bank. Total stockholders' equity declined by $663,000,  or
7.27%, principally due to the net loss realized during the period.


                                       10




                      CUMBERLAND MOUNTAIN BANCSHARES, INC.
                              Middlesboro, Kentucky

                      MANAGEMENT'S DISCUSSION AND ANALYSIS



RESULTS OF OPERATIONS

     Net Income The Company  realized a net loss of $164,000 for the three-month
     ----------
period ended December 31, 2000.  This compared to net income of $108,000 for the
three-month  period ended  December 31, 1999.  This net loss was  primarily  the
result of an increase in the  provision for loan losses of $127,000 from $98,000
for  the  three-month  period  ended  December  31,  1999  to  $225,000  for the
three-month  period ended  December 31, 2000. The increase in provision for loan
losses  is the  result  of  management's  efforts  to  increase  the  amount  of
allowances for loan losses to levels sufficient to absorb any losses suffered in
future  quarters.  Management  is continuing  their  efforts to  strengthen  the
portfolio by  tightening  underwriting  standards  and  collection  efforts.  In
addition to the increase in the provision for loan losses,  the Company incurred
other non-interest  expenses related to the write-down of foreclosed property of
$45,000 and a previously  undiscovered  reconciling  item related to the Savings
Bank's data processing  conversion of which the Savings Bank has provided a loss
provision of $125,000 during the three-month period ended December 31, 2000.

     For the six-month  period ended December 31, 2000,  the Company  realized a
net loss of  $762,000,  compared  to net income of  $274,000  for the  six-month
period  ended  December 31, 1999.  This change in net income was  primarily  the
result of an increase in provision  for loan losses of $843,000,  an increase in
provision for losses on foreclosed  real estate of $222,000 and a loss provision
of  $125,000  for  reconciling  items.   Management  believes  that  these  loss
provisions are  non-recurring  items and will benefit the  profitability  of the
Company in the long term.

     Interest  Income Total  interest  income for the  three-month  period ended
     ----------------
December 31, 2000 amounted to $2,399,000, a decrease of 1.32% from the Company's
total interest  income of $2,431,000 for the  three-month  period ended December
31, 1999.  During the three-month  period ended December 31, 2000 as compared to
the three-month period ended December 31, 1999, the Company's interest income on
its loan portfolio  decreased 0.65% from $2,295,000 to $2,280,000;  its interest
income  from its  mortgage-backed  securities  portfolio  decreased  31.25% from
$48,000 to $33,000;  interest  income from its investment  securities  portfolio
increased  21.43% from $56,000 to $68,000;  and interest  income from FHLB stock
decreased 43.75% from $32,000 to $18,000.  The decline in interest income on the
Company's  loan portfolio has occurred  primarily due to the overall  decline in
outstanding  loan balances.  This decline is primarily the result of a slow down
in origination volume combined with tighter underwriting controls.

     Interest income decreased from $4,884,000 for the six months ended December
31, 1999 to $4,877,000 for the six months ended December 31, 2000, a decrease of
$7,000 or 0.14%. This decrease resulted  primarily from the decrease in interest
income on mortgage-backed securities and FHLB Stock. Management has attempted to
increase  the  interest  income  of the  Bank  by  taking  the  repayments  from
mortgage-backed  securities and redeeming  excess FHLB stock and reinvesting the
funds in higher  yielding  mortgage,  consumer and  commercial  loans.  Interest
income on loans increased  $38,000,  or 0.83% during the six-month  period ended
December 31, 2000 as compared to the six-month  period ended  December 31, 1999.
Management  was  able to  increase  the  interest  income  on loans  during  the
six-month period primarily by reducing the amount of non-accrual loans.

     Interest  Expense  Interest  expense  increased  from  $1,466,000  for  the
     -----------------
three-month  period ended December 31, 1999, to $1,520,000  for the  three-month
period ended December 31, 2000. During the three-month period ended December 31,
2000 as  compared  to the  three-month  period  ended  December  31,  1999,  the
Company's  interest  expense on  deposits  increased  5.14% from  $1,264,000  to
$1,329,000. This increase in interest expense on deposits is due primarily to an
increase in the interest  rate paid on time deposits  resulting  from an overall
increase  in  interest  rates  from last year as well as  increased  competition
within the Company's market area.

                                       11


                      CUMBERLAND MOUNTAIN BANCSHARES, INC.
                              Middlesboro, Kentucky

                      MANAGEMENT'S DISCUSSION AND ANALYSIS



RESULTS OF OPERATIONS (CONTINUED)

     Interest  expense  increased  $124,000,  or 4.25%,  from $2,917,000 for the
six-month  period ended December 31, 1999 to $3,041,000 for the six-month period
ended  December 31,  2000.  Interest  expense on deposits  increased  5.99%,  or
$151,000 while interest expense on FHLB advances decreased 9.17%, or $30,000 for
the six-month  period ended  December 31, 2000. Due to a decrease in loans being
originated during the period,  additional  borrowings were not necessary to fund
the loan demand being experienced.

     Net Interest  Income During the three months ended  December 31, 2000,  net
     --------------------
interest  income  decreased 8.91% to $879,000 from $965,000 for the three months
ended December 31, 1999.  For the six-month  period ended December 31, 2000, net
interest  decreased 6.66% to $1,836,000 from $1,967,000 for the six-month period
ended  December 31, 1999.  This  decrease was due  primarily to the reduction in
loan growth by the Savings Bank as well as higher deposit rates.

     Provisions  for Loan  Losses  Provisions  for loan  losses  are  charged to
     ----------------------------
earnings  to  bring  the  total  allowance  to a level  considered  adequate  by
management to provide for loan losses based on the prior loss experience, volume
and type of lending  conducted by Middlesboro  Federal,  industry  standards and
past due  loans in the  Savings  Bank's  portfolio.  Management  also  considers
general economic  conditions and other factors related to the  collectibility of
the Savings Bank's portfolio.

     For the  three-month  period  ended  December  31,  2000,  the Savings Bank
provided  $225,000 for loan losses  compared to $98,000  during the  three-month
period ended  December 31, 1999.  The provision for loan losses  increased  from
$160,000 for the six months ended  December 31, 1999 to  $1,003,000  for the six
months ended  December 31, 2000.  The provision for loan loss amount  represents
management's   effort  to  maintain  an  adequate  reserve  against  losses.  In
determining the appropriate provision, management considers a number of factors,
including  specific  loans in the Savings Bank's  portfolio,  real estate market
trends in the Savings Bank's market area, economic  conditions,  interest rates,
and other  conditions  that may affect  the  borrower's  ability to comply  with
repayment  terms. At December 31, 2000, the Company's  allowance for loan losses
represented 164% of total non-accrual loans and 0.95% of the outstanding balance
of total loans.

     Non-Interest  Income  Non-interest  income for the three-month period ended
     --------------------
December  31, 2000  consisted  primarily of loan fees and service  charges.  The
Savings  Bank's loan fees and service  charges  fluctuate  as loan demand in the
market area  changes.  The  Company's  non-interest  income for the  three-month
period ended December 31, 2000 was $199,000,  an increase of 2.58% from $194,000
for  the  three-month  period  ended  December  31,  1999.  Non-interest  income
decreased  from $402,000 for the six months ended December 31, 1999 to $331,000,
a 17.66%  decline,  for the six months  ended  December  31,  2000.  Included in
non-interest  income for the  six-month  period  ended  December  31,  2000 is a
$62,000 loss on the sale of repossessed assets.

     Loan fees and service charges for the three-month period ended December 31,
2000 decreased $35,000, or 17.16%, to $169,000 from $204,000 for the three-month
period ended December 31, 1999 and $50,000,  or 12.35% for the six-month  period
ended  December 31, 2000 as compared to the six-month  period ended December 31,
1999.  This decrease was  attributable to a decrease in loan fees charged to new
loan customers during the quarter due to a reduction in origination volume.



                                       12



                      CUMBERLAND MOUNTAIN BANCSHARES, INC.
                              Middlesboro, Kentucky

                      MANAGEMENT'S DISCUSSION AND ANALYSIS



RESULTS OF OPERATIONS (CONTINUED)

     Non-Interest Expense For the three-month period ended December 31, 2000, as
     --------------------
compared to the three-month  period ended December 31, 1999, total  non-interest
expense increased  $207,000 from $905,000 to $1,112,000 or 22.87%.  Non-interest
expense  increased from $1,804,000 for the six months ended December 31, 1999 to
$2,297,000  for the six months ended  December 31, 2000, an increase of $493,000
or 27.33%.

     Total  salaries and employee  benefits  were  $384,000 for the  three-month
period ended  December 31, 2000,  up $10,000 over the  three-month  period ended
December 31, 1999 level of $374,000. For the six-month period ended December 31,
2000,  salaries and employee benefits  increased $36,000 or 4.82% as compared to
the six-month  period ended  December 31, 1999.  This increase was primarily the
result of employee salary increases. Offsetting this increase was a reduction in
SAIF  deposit  insurance  premiums  of  $11,000,  or 45.83%,  to $13,000 for the
three-month  period  ended  December  31,  2000,  compared  to  $24,000  for the
three-month  period ended  December 31, 1999.  This decrease was $22,000 for the
six-month  period ended  December 31, 2000 as compared to the  six-month  period
ended  December  31,  1999.  This  decrease  is due  mainly to the cost  savings
realized from the rate reduction by the FDIC in the Financing Corporation (FICO)
quarterly  multiplier  that took place January 1, 2000.  This  reduction set the
FICO assessment to the same rate for both BIF and SAIF insured deposits.

     Other expenses of $436,000  increased  $227,000 over the three-month period
ended  December 31, 1999 amount of $209,000.  The increase in other expenses for
the  three-month  period ending December 31, 2000, is primarily due to increases
in legal  fees,  loan  expenses,  other real  estate  owned  expenses,  and loss
provisions.  Legal fees were $9,000  higher for the  three-month  period  ending
December  31, 2000 as compared to last year due to fees  incurred in relation to
the  collection of amounts owed the Savings Bank by Blair  Mortgage  Company and
Professional  Banking  Solutions.  Loan  expenses  were  $15,000  higher for the
three-month  period ended December 31, 2000 primarily due to expenses related to
the  collection  of  delinquent  borrowers.  A loss  provision  of $125,000  was
incurred in the  three-month  period  ended  December  31,  2000 to  recognize a
potential loss from an outstanding reconciliation item as mentioned earlier.

     For the  six-month  period  ended  December 31,  2000,  other  non-interest
expenses  increased  $502,000 as compared to the six-month period ended December
31, 1999.  This  increase in other  non-interest  expenses is  primarily  due to
increases  in deposit  account  expenses,  legal  fees,  consulting  fees,  loan
expenses, other real estate owned expenses and loss provisions.  Deposit account
expenses  were  $17,000  higher  than last year due to a  one-time  expense  for
supplies  related to the conversion of the Savings Bank's  checking  services to
check imaging.  Legal fees were $28,000  higher for the six-month  period ending
December  31, 2000 as compared to last year due to fees  incurred in relation to
the  collection of amounts owed the Savings Bank by Blair  Mortgage  Company and
Professional  Banking  Solutions.  Consulting  fees  increased  $39,000  for the
six-month  period ended December 31, 2000 as compared to the three-month  period
ended  December 31,  1999.  During the quarter  ended  September  30,  2000,  an
additional  expense of $24,000  was  recognized  to adjust  for  amounts  due to
several  consulting  firms and individuals  for assistance in  implementing  the
Company's strategic plan,  performing loan review analysis,  conducting internal
audit and compliance reviews, and managing real estate development projects.



                                       13



                      CUMBERLAND MOUNTAIN BANCSHARES, INC.
                              Middlesboro, Kentucky

                      MANAGEMENT'S DISCUSSION AND ANALYSIS



RESULTS OF OPERATIONS (CONTINUED)

     Expenses  related to other real  estate  owned was  $58,000  higher for the
quarter ended  December 31, 2000 as compared to the quarter  ended  December 30,
1999 and $255,000  higher for the  six-month  period ended  December 31, 2000 as
compared to the six-month  period ended December 31, 1999.  During the six-month
period ended December 31, 2000,  the Savings Bank expensed  $9,000 for insurance
on properties  acquired  through  foreclosure,  $8,000 for the  completion of an
unfinished  duplex  acquired by the Savings  Bank,  and the value of  foreclosed
properties held by the Savings Bank were written down an additional  $222,000 to
reflect current market values.  Of the $222,000  write-down,  $188,000  directly
related to properties located in Kingsport,  Tennessee where the Savings Bank no
longer solicits business.

     Income  Taxes  The  Company   recognized  an  income  tax  credit  for  the
     -------------
three-month  period ended December 31, 2000 of $95,000 compared to an income tax
expense of $48,000 for the  three-month  period ended December 31, 1999. For the
six months  ended  December  31,  2000,  an income tax  credit of  $371,000  was
recognized  compared  to an income tax  expense of  $131,000  for the six months
ended  December  31,  1999.  The  changes in income tax  expense are a result of
changes in net taxable  income  during the periods and the change in  accounting
for tax estimates for the Company individually.

AGREEMENT AND PLAN OF SHARE EXCHANGE

     On February 8, 2001 the Company entered into an Agreement and Plan of Share
Exchange  with  Commercial  Bancgroup,  Inc.  which  provides for  Commercial to
acquire all of the issued and outstanding  shares of the Company's  common stock
for  total  consideration  of $9.52  million  (including  amounts  to be paid to
certain optionholders).  The Share Exchange,  which is subject to receipt of the
approval of the Company's  stockholders and all requisite regulatory  approvals,
is expected to be consummated in the summer of 2001.

LIQUIDITY AND CAPITAL RESOURCES

     The Company  currently has no business  other than that of the Savings Bank
and does not  currently  have any material  funding  commitments.  The Company's
principal  sources of liquidity are cash on hand,  payments received on its loan
to the Company's ESOP and dividends  received from the Savings Bank. The Savings
Bank is subject to various regulatory restrictions on the payment of dividends.

     The  Savings  Bank  is  required  by  the  Office  of  Thrift   Supervision
regulations to maintain minimum levels of specified  liquid assets.  On November
24, 1997, the OTS lowered this liquidity  requirement from 5 to 4 percent of the
Savings  Bank's   liquidity   base.   Additionally,   the  OTS  streamlined  the
calculations used to measure  compliance with liquidity  requirements,  expanded
the  types of  investments  considered  to be liquid  assets,  and  reduced  the
liquidity  base by  modifying  the  definition  of net  withdrawable  account to
exclude  accounts  with  maturities  exceeding  one  year.  The  Savings  Bank's
liquidity  ratio  for the  quarter  ended  December  31,  2000 was 6.55% and its
liquidity ratio was 7.29% at December 31, 1999.

     The  Savings  Bank's  principal   sources  of  funds  for  investments  and
operations are net income,  deposits from its primary market area, principal and
interest  payments on loans and  mortgage-backed  securities  and proceeds  from
maturing  investment  securities.  Its principal funding commitments are for the
origination or purchase of loans and the payment of maturing deposits.  Deposits
are  considered a primary  source of funds  supporting the Savings Banks lending
and  investment  activities.  Deposits were  $104,159,000  and  $106,078,000  at
December 31, 2000 and June 30, 2000, respectively.



                                       14


                      CUMBERLAND MOUNTAIN BANCSHARES, INC.
                              Middlesboro, Kentucky

                      MANAGEMENT'S DISCUSSION AND ANALYSIS



LIQUIDITY AND CAPITAL RESOURCES (CONTINUED)

     The Savings Bank's most liquid assets are cash and cash equivalents,  which
are cash on hand, amounts due from financial  institutions,  federal funds sold,
certificates of deposit with other financial  institutions that have an original
maturity of three months or less and money market  mutual  funds.  The levels of
such  assets are  dependent  on the  Savings  Bank's  operating,  financing  and
investment  activities  at any given  time.  The  Savings  Bank's  cash and cash
equivalents  totaled  $5,038,000 at December 31, 2000 and $1,581,000 at June 30,
2000.  Of  these  amounts,  $2,340,000  and  $1,069,000  were  deposits  held in
interest-bearing  accounts at December 31, 2000 and June 30, 2000, respectively.
The variations in levels of cash and cash  equivalents are influenced by deposit
flows and anticipated future deposit flows.

     At December 31,  2000,  the Savings  Bank had  $209,000 in  commitments  to
originate  loans.  At December 31, 2000,  the Savings  Bank had  $58,665,000  in
certificates  of deposit which were  scheduled to mature in one year or less. It
is anticipated  that the majority of these  certificates  will be renewed in the
normal course of operations.

     Middlesboro  Federal is not aware of any trends or uncertainties  that will
have or are reasonably  expected to have a material effect on the Savings Bank's
liquidity  or capital  resources.  The  Savings  Bank has no  current  plans for
material capital  improvements or other capital  expenditures that would require
more funds than are currently on hand.


IMPACT OF INFLATION AND CHANGING PRICES

     The  financial  statements  and  related  data  presented  herein have been
prepared in accordance  with  generally  accepted  accounting  principles  which
require the measurement of financial  position and operating results in terms of
historical dollars, without considering changes in the relative purchasing power
of money over time due to inflation.

     Unlike  most   companies,   the  assets  and  liabilities  of  a  financial
institution are primarily monetary in nature. As a result, interest rates have a
more  significant  impact  on a  financial  institution's  performance  than the
effects of general levels of inflation.  Interest rates do not necessarily  move
in the  same  direction  or in the same  magnitude  as the  price  of goods  and
services,  since such prices are affected by inflation.  In the current interest
rate  environment,  liquidity and the maturity  structure of the Savings  Bank's
assets and liabilities are critical to the maintenance of acceptable performance
levels.

NEW ACCOUNTING PRONOUNCEMENTS

     Disclosures About Fair Value of Financial Instruments In December 1991, the
     -----------------------------------------------------
FASB issued Statement of Financial  Accounting  Standards No. 107 (SFAS No. 107)
"Disclosure  About Fair Value of Financial  Instruments."  SFAS No. 107 requires
all entities to disclose the fair value of  financial  instruments  (both assets
and liabilities  recognized and not recognized in the financial  statements) for
which  it  is  practicable  to  estimate  fair  value,  except  those  financial
instruments specifically excluded. The disclosure shall be either in the body of
the financial statements or in the accompanying notes and shall also include the
methods and significant assumptions used to estimate the fair value of financial
instruments.  Additional  information  is required to be  disclosed if it is not
practicable  for an entity to estimate the fair value of a financial  instrument
or a  class  of  financial  instruments  as well  as the  reasons  why it is not
practicable to estimate fair value.  SFAS No. 107 is effective for entities with
less than $150  million in total  assets in the current  statement  of financial
condition for financial  statements issued for the fiscal year beginning July 1,
1995.


                                       15


                      CUMBERLAND MOUNTAIN BANCSHARES, INC.
                              Middlesboro, Kentucky

                      MANAGEMENT'S DISCUSSION AND ANALYSIS



NEW ACCOUNTING PRONOUNCEMENTS (CONTINUED)

     Accounting By Creditors For  Impairment of a Loan During May 1993, the FASB
     -------------------------------------------------
issued SFAS No. 114  "Accounting  by Creditors  for  Impairment  of a Loan" that
requires  impaired  loans be measured  based upon the present  value of expected
future cash flows  discounted  at the loan's  effective  interest rate or at the
loan's  market  price or fair  value of  collateral,  if the loan is  collateral
dependent.  Adoption of SFAS No.  114,  as amended by SFAS No. 118,  occurred on
June  30,  1996,  and is  did  not  have  a  material  impact  on the  financial
statements.

     Earnings  Per Share In  February  1997,  the FASB issued SFAS No. 128 which
    --------------------
requires  companies  to present  basic  earnings  per share and, if  applicable,
diluted  earnings per share,  instead of primary and fully diluted  earnings per
share,  respectively.  Basic earnings per share are computed  without  including
potential common shares, i.e. no dilutive effect.  Diluted earnings per share is
computed  taking into  consideration  common  shares  outstanding  and  dilutive
potential common shares,  including options,  warrants,  convertible securities,
and contingent  stock  agreements.  SFAS No. 128 is effective for periods ending
after December 15, 1997.

     Comprehensive  Income  In  June,  1997,  the  FASB  issued  SFAS  No.  130,
     ---------------------
"Reporting  Comprehensive  Income".  SFAS  No.  130  establishes  standards  for
reporting  and display of  comprehensive  income and its  components  (revenues,
expenses,  gains,  and  losses)  in a  full  set  of  general-purpose  financial
statements.  This  statement  requires  that all items that are  required  to be
recognized under accounting  standards as components of comprehensive  income be
reported in a financial  statement that is displayed with the same prominence as
other financial statements.

     This  statement  requires  that an enterprise  (a) classify  items of other
comprehensive  income by their nature in a financial  statement  and (b) display
the accumulated balance of other  comprehensive  income separately from retained
earnings and additional  paid-in capital in the equity section of a statement of
financial position. This statement is effective for fiscal years beginning after
December 15, 1997.

     Disclosures  about  Segments of an Enterprise  and Related  Information  In
     -----------------------------------------------------------------------
June,  1997,  the FASB issued SFAS No. 131,  "Disclosures  about  Segments of an
Enterprise and Related Information".  SFAS No. 131 establishes standards for the
way that public business enterprises report information about operating segments
in annual  financial  statements  and  requires  that those  enterprises  report
selected  information  about  operating  segments in interim  financial  reports
issued to shareholders.  It also establishes  standards for related  disclosures
about  products  and  services,  geographic  areas,  and major  customers.  This
statement is effective  for financial  statements  for periods  beginning  after
December  15,  1997.  The  Company  does not believe  that the  adoption of this
accounting statement will have a material impact on its financial statements.



                                       16


                      CUMBERLAND MOUNTAIN BANCSHARES, INC.
                              Middlesboro, Kentucky

                           PART II. OTHER INFORMATION



Item 1.  LEGAL PROCEEDINGS
         -----------------

     From time to time  between  1987 and 1994 the  Savings  Bank has  purchased
whole loans and loan participations  from an unaffiliated  mortgage broker based
in Lexington,  Kentucky.  The mortgage  broker had been servicing such loans for
the Savings Bank remitting payments on a monthly basis.  During the three months
ended  September 30, 1999, the Savings Bank became aware that certain such loans
might have been  refinanced  although  the mortgage  broker  failed to remit the
payoffs on such loans to the Savings  Bank.  At March 31,  2000,  the  aggregate
principal balance of such loans amounted to $668,000. The Savings Bank has begun
to  service  all such  loans  directly  and is  pursuing  a claim for the unpaid
principal balance with its fidelity insurance carrier. Although the Savings Bank
believes  it has a claim  under its  fidelity  bond or through  other  insurance
policies, there can be no assurance that full or partial recovery of these loans
will be obtained or that loss in connection with these loans will be incurred.

Item 4.  SUBMISSION OF MATTERS TO A VOTE OF SECURITY-HOLDERS
         ---------------------------------------------------

     On October 18, 2000, the Registrant held its Annual Meeting of Stockholders
of the purpose of electing directors.  All matters were approved. The results of
the voting at the Annual Meeting were as follows:

PROPOSAL I - ELECTION OF DIRECTORS

         NOMINEE                         VOTES FOR         VOTES WITHHELD

         J. Roy Shoffner                 537,904            13,257


Item 5.  Other Information
         -----------------

     Effective  December  13,  1999,  the Savings Bank entered into an Agreement
with the Office of Thrift  Supervision.  The Agreement requires that the Savings
Bank  establish  the  position  of  Compliance  Officer  and develop and adopt a
written  compliance  program designed to ensure the Savings Bank is operating in
compliance  with  all  applicable   consumer   protection  and  other  laws  and
regulations. The Savings Bank is also required to ensure its compliance with its
written loan and collection  policies.  The Agreement limits the size of any new
commercial  loans to $100,000 and any unsecured  consumer loans to $25,000.  The
Savings Bank was also required to modify its existing  strategic plan and budget
to reflect these  requirements and was required to make certain filings with the
OTS in accordance with deadlines established in the Agreement.  The Savings Bank
does not believe that the terms of this Agreement  will have a material  adverse
effect on the Savings Bank.

Item 6.  Exhibits and Reports on Form 8-K
         --------------------------------

         (a)      Exhibits. None
                  --------

         (b)      Reports on Form 8-K.   During the quarter ended December 31,
                  -------------------
2000, the registrant did not file any reports on Form 8-K.


                                       17



                      CUMBERLAND MOUNTAIN BANCSHARES, INC.
                              Middlesboro, Kentucky

                                   SIGNATURES



Pursuant  to the  requirements  of the  Securities  Exchange  Act of  1934,  the
registrant  has duly  caused  this  report  to be  signed  on its  behalf by the
undersigned, thereunto duly authorized.



                                       Cumberland Mountain Bancshares, Inc.



                                       By:/s/ James J. Shoffner
                                          ---------------------------------
                                          James J. Shoffner
                                          President


Date:  February 13, 2001