| 7. Round | 27/09/2008 | Dundee United | - | Heart of Midlothian | 3:0 | ||||
| 8. Round | 04/10/2008 | Heart of Midlothian | - | Kilmarnock FC | 1:2 | ||||
| 30. Round | 21/03/2009 | Rangers FC | - | Heart of Midlothian | 2:2 |  |
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| 31. Round | 04/04/2009 | Heart of Midlothian | - | Kilmarnock FC | 3:1 | ||||
| 32. Round | 11/04/2009 | Heart of Midlothian | - | Celtic FC | 1:1 |
Denmark