| 10. Round | 25/10/2008 | Hamilton Academical | - | Rangers FC | 1:3 | ||||
| 13. Round | 12/11/2008 | Heart of Midlothian | - | Hamilton Academical | 1:0 | ||||
| 16. Round | 29/11/2008 | Hamilton Academical | - | Kilmarnock FC | 1:0 | ||||
| 17. Round | 06/12/2008 | Rangers FC | - | Hamilton Academical | 7:1 | ||||
| 21. Round | 03/01/2009 | Hamilton Academical | - | Aberdeen FC | 2:0 | ||||
| 26. Round | 21/02/2009 | Falkirk FC | - | Hamilton Academical | 1:2 | ||||
| 27. Round | 28/02/2009 | Hamilton Academical | - | Rangers FC | 0:1 | ||||
| 28. Round | 04/03/2009 | Hamilton Academical | - | Hibernian FC | 0:1 | ||||
| 29. Round | 14/03/2009 | Aberdeen FC | - | Hamilton Academical | 1:0 | ||||
| 30. Round | 21/03/2009 | Hamilton Academical | - | St. Mirren FC | 0:0 | ||||
| 31. Round | 04/04/2009 | Celtic FC | - | Hamilton Academical | 4:0 | ||||
| 32. Round | 11/04/2009 | Hamilton Academical | - | Dundee United | 0:1 | ||||
| 33. Round | 18/04/2009 | Inverness CT | - | Hamilton Academical | 1:1 |  |
Scotland