| 3. Journée | 16.08.2008 | St. Johnstone FC | - | Dunfermline Athletic | 0:3 |  |
|||
| 7. Journée | 20.09.2008 | Dunfermline Athletic | - | Ross County FC | 3:1 | |
|||
| 11. Journée | 04.11.2008 | Airdrie United FC | - | Dunfermline Athletic | 1:3 | |
|||
| 17. Journée | 13.12.2008 | Queen Of The South | - | Dunfermline Athletic | 1:2 | |
|||
| 18. Journée | 20.12.2008 | Dunfermline Athletic | - | Clyde FC | 4:4 | |
|||
| 30. Journée | 21.03.2009 | Clyde FC | - | Dunfermline Athletic | 1:4 | |
|||
| 35. Journée | 02.05.2009 | Queen Of The South | - | Dunfermline Athletic | 0:3 | |
Écosse