1. Round | 09/08/2008 | Heart of Midlothian | - | Motherwell FC | 3:2 | ||||
8. Round | 04/10/2008 | Heart of Midlothian | - | Kilmarnock FC | 1:2 | ||||
14. Round | 15/11/2008 | Inverness CT | - | Heart of Midlothian | 0:1 | ||||
15. Round | 22/11/2008 | Heart of Midlothian | - | Falkirk FC | 2:1 |