1. Round | 11/08/2008 | Hamilton Academical | - | Dundee United | 3:1 | ||||
2. Round | 16/08/2008 | Inverness CT | - | Hamilton Academical | 0:1 | ||||
4. Round | 30/08/2008 | Hamilton Academical | - | Heart of Midlothian | 1:2 | ||||
5. Round | 13/09/2008 | Aberdeen FC | - | Hamilton Academical | 1:2 | ||||
9. Round | 18/10/2008 | Hamilton Academical | - | St. Mirren FC | 1:2 | ||||
10. Round | 25/10/2008 | Hamilton Academical | - | Rangers FC | 1:3 | ||||
12. Round | 08/11/2008 | Hamilton Academical | - | Falkirk FC | 1:1 | ||||
13. Round | 12/11/2008 | Heart of Midlothian | - | Hamilton Academical | 1:0 | ||||
15. Round | 22/11/2008 | Dundee United | - | Hamilton Academical | 1:1 | ||||
16. Round | 29/11/2008 | Hamilton Academical | - | Kilmarnock FC | 1:0 | ||||
22. Round | 17/01/2009 | Hamilton Academical | - | Inverness CT | 1:0 |