3. Round | 16/08/2008 | St. Johnstone FC | - | Dunfermline Athletic | 0:3 | ||||
7. Round | 20/09/2008 | Dunfermline Athletic | - | Ross County FC | 3:1 | ||||
11. Round | 04/11/2008 | Airdrie United FC | - | Dunfermline Athletic | 1:3 | ||||
17. Round | 13/12/2008 | Queen Of The South | - | Dunfermline Athletic | 1:2 | ||||
18. Round | 20/12/2008 | Dunfermline Athletic | - | Clyde FC | 4:4 | ||||
30. Round | 21/03/2009 | Clyde FC | - | Dunfermline Athletic | 1:4 | ||||
35. Round | 02/05/2009 | Queen Of The South | - | Dunfermline Athletic | 0:3 |