1. Round | 11/08/2008 | Hamilton Academical | - | Dundee United | 3:1 | ||||
2. Round | 16/08/2008 | Inverness CT | - | Hamilton Academical | 0:1 | ||||
3. Round | 23/08/2008 | Kilmarnock FC | - | Hamilton Academical | 1:0 | ||||
4. Round | 30/08/2008 | Hamilton Academical | - | Heart of Midlothian | 1:2 | ||||
5. Round | 13/09/2008 | Aberdeen FC | - | Hamilton Academical | 1:2 | ||||
7. Round | 27/09/2008 | Falkirk FC | - | Hamilton Academical | 4:1 | ||||
20. Round | 27/12/2008 | St. Mirren FC | - | Hamilton Academical | 1:0 |