3. Round | 16/08/2008 | St. Johnstone FC | - | Dunfermline Athletic | 0:3 | ||||
14. Round | 15/11/2008 | Livingston FC | - | Dunfermline Athletic | 2:3 | ||||
17. Round | 13/12/2008 | Queen Of The South | - | Dunfermline Athletic | 1:2 | ||||
25. Round | 21/02/2009 | Dunfermline Athletic | - | Ross County FC | 1:2 | ||||
16. Round | 24/03/2009 | Ross County FC | - | Dunfermline Athletic | 2:1 | ||||
33. Round | 18/04/2009 | Ross County FC | - | Dunfermline Athletic | 1:3 |