| 2. Journée | 09.08.2008 | Dunfermline Athletic | - | Queen Of The South | 2:1 |  |
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| 5. Journée | 30.08.2008 | Dunfermline Athletic | - | Livingston FC | 1:2 | |
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| 9. Journée | 04.10.2008 | Clyde FC | - | Dunfermline Athletic | 0:2 | |
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| 10. Journée | 18.10.2008 | Dunfermline Athletic | - | Partick Thistle | 1:0 | |
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| 14. Journée | 15.11.2008 | Livingston FC | - | Dunfermline Athletic | 2:3 | |
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| 18. Journée | 20.12.2008 | Dunfermline Athletic | - | Clyde FC | 4:4 | |
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| 24. Journée | 14.02.2009 | Partick Thistle | - | Dunfermline Athletic | 2:3 | |
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| 26. Journée | 28.02.2009 | Greenock Morton FC | - | Dunfermline Athletic | 2:1 | |
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| 32. Journée | 11.04.2009 | Dunfermline Athletic | - | St. Johnstone FC | 1:3 | |
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| 33. Journée | 18.04.2009 | Ross County FC | - | Dunfermline Athletic | 1:3 | |
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| 35. Journée | 02.05.2009 | Queen Of The South | - | Dunfermline Athletic | 0:3 | |
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| 34. Journée | 05.05.2009 | Dunfermline Athletic | - | Greenock Morton FC | 2:1 | |
Irlande du Nord