1. Round | 09/08/2008 | Aberdeen FC | - | Inverness CT | 0:2 | ||||
2. Round | 16/08/2008 | Inverness CT | - | Hamilton Academical | 0:1 | ||||
3. Round | 23/08/2008 | Inverness CT | - | Hibernian FC | 1:1 | ||||
4. Round | 30/08/2008 | Falkirk FC | - | Inverness CT | 1:2 | ||||
5. Round | 13/09/2008 | Inverness CT | - | St. Mirren FC | 1:2 | ||||
6. Round | 20/09/2008 | Heart of Midlothian | - | Inverness CT | 1:0 | ||||
7. Round | 27/09/2008 | Inverness CT | - | Kilmarnock FC | 3:1 | ||||
9. Round | 18/10/2008 | Inverness CT | - | Celtic FC | 1:2 | ||||
18. Round | 13/12/2008 | St. Mirren FC | - | Inverness CT | 2:0 | ||||
20. Round | 27/12/2008 | Motherwell FC | - | Inverness CT | 3:2 | ||||
23. Round | 24/01/2009 | Heart of Midlothian | - | Inverness CT | 3:2 |