1. Round | 09/08/2008 | Heart of Midlothian | - | Motherwell FC | 3:2 | ||||
2. Round | 16/08/2008 | Rangers FC | - | Heart of Midlothian | 2:0 | ||||
3. Round | 23/08/2008 | Heart of Midlothian | - | St. Mirren FC | 2:1 | ||||
8. Round | 04/10/2008 | Heart of Midlothian | - | Kilmarnock FC | 1:2 | ||||
9. Round | 19/10/2008 | Hibernian FC | - | Heart of Midlothian | 1:1 | ||||
12. Round | 08/11/2008 | St. Mirren FC | - | Heart of Midlothian | 0:1 | ||||
21. Round | 03/01/2009 | Heart of Midlothian | - | Hibernian FC | 0:0 | ||||
22. Round | 17/01/2009 | Kilmarnock FC | - | Heart of Midlothian | 0:2 | ||||
26. Round | 21/02/2009 | Heart of Midlothian | - | St. Mirren FC | 1:1 |