3. Round | 23/08/2008 | Heart of Midlothian | - | St. Mirren FC | 2:1 | ||||
4. Round | 30/08/2008 | Hamilton Academical | - | Heart of Midlothian | 1:2 | ||||
5. Round | 13/09/2008 | Falkirk FC | - | Heart of Midlothian | 2:1 | ||||
6. Round | 20/09/2008 | Heart of Midlothian | - | Inverness CT | 1:0 | ||||
7. Round | 27/09/2008 | Dundee United | - | Heart of Midlothian | 3:0 | ||||
8. Round | 04/10/2008 | Heart of Midlothian | - | Kilmarnock FC | 1:2 | ||||
9. Round | 19/10/2008 | Hibernian FC | - | Heart of Midlothian | 1:1 | ||||
33. Round | 18/04/2009 | Falkirk FC | - | Heart of Midlothian | 0:0 |