| 3. Jornada | 16.08.2008 | St. Johnstone FC | - | Dunfermline Athletic | 0:3 |  |
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| 14. Jornada | 15.11.2008 | Livingston FC | - | Dunfermline Athletic | 2:3 | |
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| 17. Jornada | 13.12.2008 | Queen Of The South | - | Dunfermline Athletic | 1:2 | |
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| 25. Jornada | 21.02.2009 | Dunfermline Athletic | - | Ross County FC | 1:2 | |
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| 16. Jornada | 24.03.2009 | Ross County FC | - | Dunfermline Athletic | 2:1 | |
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| 33. Jornada | 18.04.2009 | Ross County FC | - | Dunfermline Athletic | 1:3 | |
Escocia