| 1. Round | 29/07/2006 | Dunfermline Athletic | - | Heart of Midlothian | 1:2 | ||||
| 2. Round | 06/08/2006 | Heart of Midlothian | - | Celtic FC | 2:1 | ||||
| 3. Round | 12/08/2006 | Heart of Midlothian | - | Falkirk FC | 0:0 | ||||
| 4. Round | 19/08/2006 | Rangers FC | - | Heart of Midlothian | 2:0 |  |
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| 5. Round | 26/08/2006 | Heart of Midlothian | - | Inverness CT | 4:1 | ||||
| 6. Round | 09/09/2006 | Heart of Midlothian | - | St. Mirren FC | 0:1 | ||||
| 7. Round | 17/09/2006 | Motherwell FC | - | Heart of Midlothian | 0:1 | ||||
| 8. Round | 24/09/2006 | Aberdeen FC | - | Heart of Midlothian | 1:3 | |
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| 9. Round | 01/10/2006 | Heart of Midlothian | - | Dundee United | 4:0 | ||||
| 10. Round | 15/10/2006 | Hibernian FC | - | Heart of Midlothian | 2:2 | |
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| 11. Round | 21/10/2006 | Heart of Midlothian | - | Kilmarnock FC | 0:2 | ||||
| 12. Round | 28/10/2006 | Heart of Midlothian | - | Dunfermline Athletic | 1:1 | ||||
| 16. Round | 25/11/2006 | Inverness CT | - | Heart of Midlothian | 0:0 |
Scotland