FIFTH AMENDMENT TO SEVENTH RESTATED CREDIT AGREEMENT

FIFTH AMENDMENT TO SEVENTH RESTATED CREDIT AGREEMENT

This Fifth Amendment to Seventh Restated Credit Agreement (this “ Fifth Amendment ”) is effective as of May 21, 2009 (the “ Fifth Amendment Effective Date ”), by and among CHAPARRAL ENERGY, INC. , a Delaware corporation (“ Parent ”), CHAPARRAL ENERGY, L.L.C. , an Oklahoma limited liability company (in its capacity as Borrower Representative for the Borrowers, “ Borrower Representative ”), JPMORGAN CHASE BANK, N.A. , a national banking association, as Administrative Agent (“ Administrative Agent ”), and each of the financial institutions a party hereto as Lenders (hereinafter collectively referred to as “ Lenders ”, and individually, “ Lender ”).

W I T N E S S E T H :

WHEREAS, Parent, Borrowers, Administrative Agent, the other Agents party thereto and Lenders are parties to that certain Seventh Restated Credit Agreement dated as of October 31, 2006 (as amended, the “ Credit Agreement ”) (unless otherwise defined herein, all terms used herein with their initial letter capitalized shall have the meaning given such terms in the Credit Agreement); and

WHEREAS, pursuant to the Credit Agreement, the Lenders have made revolving credit loans to Borrowers; and

WHEREAS, the parties hereto desire to (a) amend certain terms of the Credit Agreement in certain respects, and (b) reaffirm the Borrowing Base in an amount equal to $600,000,000, to be effective as of the Fifth Amendment Effective Date and continuing until the next redetermination of the Borrowing Base thereafter.

NOW THEREFORE, for and in consideration of the mutual covenants and agreements herein contained and other good and valuable consideration, the receipt and sufficiency of which are hereby acknowledged and confessed, Parent, Borrower Representative (on behalf of Borrowers), Administrative Agent and Lenders hereby agree as follows:

SECTION 1. Amendments . In reliance on the representations, warranties, covenants and agreements contained in this Fifth Amendment, and subject to the satisfaction of the conditions precedent set forth in Section 3 hereof, the Credit Agreement is hereby amended effective as of the Fifth Amendment Effective Date in the manner provided in this Section 1 .

1.1        Amended and Restated Definitions . The definitions of “ Applicable Margin ”, “ Consolidated EBITDAX ”, “ Consolidated Senior Total Debt ”, “ Loan Documents ”, “ Mandatory Redetermination ” and “ Mandatory Redetermination Date ” contained in Section 1.02 of the Credit Agreement shall be amended to read in full as follows:

“ Applicable Margin ” means, for any day, with respect to any ABR Loan or Eurodollar Loan, or with respect to the Commitment Fee Rate, as the case may be, the rate per annum set forth in the Conforming Borrowing Base Utilization Grid below based upon the Conforming Borrowing Base Utilization Percentage then in effect:

Each change in the Applicable Margin shall apply during the period commencing on the effective date of such change and ending on the date immediately preceding the effective date of the next such change.

“ Consolidated EBITDAX ” means with respect to Parent and the Consolidated Subsidiaries for any applicable period: (a) Consolidated Net Income of Parent and the Consolidated Subsidiaries for such period, plus, to the extent deducted in the calculation of Consolidated Net Income, (b) the sum of (i) income or material franchise Taxes paid or accrued; (ii) Consolidated Net Interest Expense; (iii) amortization, depletion and depreciation expense; (iv) any non-cash losses or charges on any Swap Agreement, including those resulting from the requirements of FASB 133, for that period; (v) other non-cash charges (excluding accruals for cash expenses made in the ordinary course of business), including, without limitation, non-cash employee compensation; and (vi) costs and expenses associated with, and attributable to, oil and gas capital expenditures that are expensed rather than capitalized; less, to the extent included in the calculation of Consolidated Net Income, (c) the sum of (i) the income of any Person (other than Wholly-Owned Subsidiaries of such Person) unless such income is received by such Person in a cash distribution; (ii) gains or losses from sales or other dispositions of assets (other than Hydrocarbons produced in the normal course of business); (iii) any non-cash gains on any Swap Agreement, including those resulting from the requirements of FASB 133, for that period; (iv) any cash proceeds received from the termination or other monetization of any Swap Agreement with a scheduled maturity date more than 12 months following the date of such termination or other monetization, including, without limitation, any cash proceeds received from any Specified Hedge Monetization and (v) extraordinary or non-recurring gains, but not net of extraordinary or non-recurring “cash” losses. Notwithstanding anything to the contrary contained herein, all calculations of Consolidated EBITDAX shall be (A) in all respects, acceptable to, and approved by, the Administrative Agent, (B) for any applicable period of determination during which a Credit Party has consummated an acquisition or disposition (to the extent permitted hereunder) of Properties, calculated and determined on a pro forma basis as if such acquisition or disposition was consummated on the first day of such applicable period, and (C) calculated, determined and adjusted for any applicable period to exclude any income, loss or other adjustments with respect to Chaparral Biofuels, Oklahoma Ethanol and Pointe Vista determined in accordance with GAAP, except income received pursuant to a cash distribution shall be included in the calculation of Consolidated EBITDAX.

“ Consolidated Senior Total Debt ” means, with respect to Parent and the Consolidated Subsidiaries for any period, (a) all Funded Debt of Parent and the Consolidated Subsidiaries determined on a consolidated basis for such period, other than Permitted Bond Debt minus (b) Excess Cash on the date of calculation.

“ Loan Documents ” means this Agreement, the First Amendment, the Second Amendment, the Third Amendment, the Fourth Amendment, the Fifth Amendment, the Notes, the Letter of Credit Agreements, the Letters of Credit, the Certificate of Effectiveness, and the Security Instruments.

“ Mandatory Redetermination ” means any redetermination of the Borrowing Base and Conforming Borrowing Base under Section 2.07(d) or Section 2.10(a).

“ Mandatory Redetermination Date ” means the date on which a Borrowing Base and, as applicable, Conforming Borrowing Base that has been redetermined pursuant to a Mandatory Redetermination under Section 2.07(d)(iii) or under Section 2.10(a) becomes effective as provided under Section 2.07(e)(iv) or Section 2.10(b) as applicable.

1.2        Additional Definitions . Section 1.02 of the Credit Agreement shall be amended to add the following definitions to such Section:

“ Capital Expenditures ” means, without duplication, any expenditure or commitment to expend money for any purchase or other acquisition of any asset which would be classified as a fixed or capital asset on a balance sheet of Parent, the Borrowers or any other Credit Party prepared in accordance with GAAP and any other capital expenditure determined in accordance with GAAP including, without limitation, replacements, capitalized repairs and improvements, capitalized interest and capitalized general and administrative expenses.

“ Discretionary Cash Flows ” means with respect to Parent and the Consolidated Subsidiaries for any applicable period: (a) Consolidated EBITDAX for such period minus (b) Consolidated Net Interest Expense for such period minus (c) the amount of income and material franchise Taxes paid in cash during such period.

“ Excess Available Cash ” means Excess Cash plus the amount, if any, by which the total Commitments exceed the total Credit Exposures (but only to the extent that the Borrowers are permitted to borrow such amount under the terms of this Agreement including, without limitation, Section 6.02 hereof).

“ Excess Cash ” means the amount, if any, that (a) the sum of (i) Parent’s and the Consolidated Subsidiaries’ cash on hand plus (ii) the aggregate amount of Parent’s and the Consolidated Subsidiaries’ Investments of the types described in clauses (c), (d), (e) and (f) of Section 9.05 exceeds (b) the aggregate amount of the Credit Parties’ accounts payable and accrued expenses, liabilities or other obligations to pay the deferred purchase price of Property or services that are

greater than ninety (90) days past the date of invoice unless such accounts payable, expenses, liabilities or other obligations are being contested in good faith by appropriate action and for which adequate reserves have been maintained in accordance with GAAP.

“ Fifth Amendment ” means that certain Fifth Amendment to Seventh Restated Credit Agreement dated effective as May 21, 2009, among Parent, Borrower Representative (on behalf of Borrowers), Administrative Agent and Lenders.

“ Fifth Amendment Effective Date ” has the meaning ascribed to such term in the Fifth Amendment.

“ Net Proceeds ” means, with respect to any event, (a) the cash proceeds received in respect of such event including any cash received in respect of any non-cash proceeds (including any cash payments received by way of deferred payment of principal pursuant to a note or installment receivable or purchase price adjustment receivable or otherwise, but excluding any interest payments), but only as and when received, net of (b) the sum of (i) all reasonable fees and out-of-pocket expenses paid to third parties (other than Affiliates) in connection with such event, (ii) in the case of a sale, transfer or other disposition of an asset (including pursuant to a sale and leaseback transaction or a casualty or a condemnation or similar proceeding), the amount of all payments required to be made as a result of such event to repay Debt (other than Loans) secured by such asset or otherwise subject to mandatory prepayment as a result of such event and (iii) the amount of all taxes paid (or reasonably estimated to be payable) and the amount of any reserves established to fund contingent liabilities reasonably estimated to be payable, in each case during the year that such event occurred or the next succeeding year and that are directly attributable to such event (as determined reasonably and in good faith by a Financial Officer).

“ Specified Hedge Monetization ” means any termination or monetization of any Swap Agreement listed on Schedule 1 to the Fifth Amendment that is so terminated or monetized on or prior to November 1, 2009.

“ Specified Hedge Monetization Date ” means any date on which a Credit Party receives Net Proceeds from a Specified Hedge Monetization.

1.3        Additional Mandatory Redetermination Provision . A new Section 2.10 shall be added to the Credit Agreement and read as follows:

(a)       In addition to other redeterminations of the Borrowing Base and Conforming Borrowing Base provided for herein, and notwithstanding anything to the contrary contained herein, the Borrowing Base and Conforming Borrowing Base shall each automatically reduce promptly, but in no event more than two (2) Business Days, following any Specified Hedge Monetization Date by an amount,

with respect to each of the Borrowing Base and Conforming Borrowing Base, equal to eighty-five percent (85%) of the aggregate Net Proceeds received by the Credit Parties from Specified Hedge Monetizations on such Specified Hedge Monetization Date.

(b)       After a redetermined Borrowing Base and/or Conforming Borrowing Base is automatically adjusted pursuant to Section 2.10(a), the Administrative Agent shall deliver to the Borrowers (or Borrower Representative) and the Lenders a New Borrowing Base Notice, and such amount as set forth in such New Borrowing Base Notice shall become the new Borrowing Base and/or Conforming Borrowing Base, effective and applicable to the Borrowers, the Agents, each Issuing Bank and the Lenders on the applicable Mandatory Redetermination Date, regardless of the date of delivery of such New Borrowing Base Notice.”

1.4        Amendment to Mandatory Prepayments Provision . Clause (iii) of Section 3.04(c) of the Credit Agreement shall be amended to delete the reference therein to “Section 2.07(d),” and insert in lieu thereof a reference to “Section 2.07(d) or Section 2.10(a),”.

1.5        Amendment to Use of Proceeds Representation . Section 7.21 of the Credit Agreement shall be amended and restated in its entirety as follows:

“Section 7.21   Use of Loans and Letters of Credit . The proceeds of the Loans and the Letters of Credit shall be used to refinance existing indebtedness, to finance the Calumet Acquisition, to provide working capital for exploration and production, and for general corporate purposes of the Borrowers and their Subsidiaries, including the acquisition of exploration and production properties. No Credit Party is engaged principally, or as one of its important activities, in the business of extending credit for the purpose, whether immediate, incidental or ultimate, of buying or carrying margin stock (within the meaning of Regulation T, U or X of the Board). No part of the proceeds of any Loan or Letter of Credit will be used for any purpose which violates the provisions of Regulations T, U or X of the Board. No part of the proceeds of any Loan or Letter of Credit will be used for the purpose of making payments of the type permitted under clause (d) of Section 9.04.”

1.6        Amendment to Financial Statements; Other Information Provision . A new paragraph (m) shall be added at the end of Section 8.01 of the Credit Agreement and read in full as follows:

“(m)     Statement of Capital Expenditures and Discretionary Cash Flows . For the three month period of Parent ending June 30, 2009, the six month period of Parent ending September 30, 2009 and the nine month period of Parent ending December 31, 2009, concurrently with any delivery of financial statements under Section 8.01(a) or Section 8.01(b), a statement of the Credit Parties’ Capital Ex