| 2. Round | 09/08/2008 | Dunfermline Athletic | - | Queen Of The South | 2:1 |  |
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| 5. Round | 30/08/2008 | Dunfermline Athletic | - | Livingston FC | 1:2 | |
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| 9. Round | 04/10/2008 | Clyde FC | - | Dunfermline Athletic | 0:2 | |
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| 10. Round | 18/10/2008 | Dunfermline Athletic | - | Partick Thistle | 1:0 | |
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| 14. Round | 15/11/2008 | Livingston FC | - | Dunfermline Athletic | 2:3 | |
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| 18. Round | 20/12/2008 | Dunfermline Athletic | - | Clyde FC | 4:4 | |
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| 24. Round | 14/02/2009 | Partick Thistle | - | Dunfermline Athletic | 2:3 | |
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| 26. Round | 28/02/2009 | Greenock Morton FC | - | Dunfermline Athletic | 2:1 | |
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| 32. Round | 11/04/2009 | Dunfermline Athletic | - | St. Johnstone FC | 1:3 | |
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| 33. Round | 18/04/2009 | Ross County FC | - | Dunfermline Athletic | 1:3 | |
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| 35. Round | 02/05/2009 | Queen Of The South | - | Dunfermline Athletic | 0:3 | |
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| 34. Round | 05/05/2009 | Dunfermline Athletic | - | Greenock Morton FC | 2:1 | |
Northern Ireland