3. Round | 16/08/2008 | Clyde FC | - | Ross County FC | 2:2 | ||||
5. Round | 30/08/2008 | Partick Thistle | - | Ross County FC | 0:1 | ||||
7. Round | 20/09/2008 | Dunfermline Athletic | - | Ross County FC | 3:1 | ||||
8. Round | 27/09/2008 | Ross County FC | - | Airdrie United FC | 2:0 | ||||
9. Round | 04/10/2008 | Ross County FC | - | Greenock Morton FC | 3:0 | ||||
10. Round | 18/10/2008 | Dundee FC | - | Ross County FC | 1:2 | ||||
20. Round | 07/02/2009 | Ross County FC | - | St. Johnstone FC | 2:2 | ||||
33. Round | 18/04/2009 | Ross County FC | - | Dunfermline Athletic | 1:3 | ||||
35. Round | 02/05/2009 | Ross County FC | - | Livingston FC | 2:2 |