| 1. Round | 07/08/2004 | Dundee FC | - | Heart of Midlothian | 0:1 | ||||
| 2. Round | 14/08/2004 | Heart of Midlothian | - | Aberdeen FC | 0:0 |  |
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| 3. Round | 21/08/2004 | Heart of Midlothian | - | Kilmarnock FC | 3:0 | ||||
| 4. Round | 28/08/2004 | Motherwell FC | - | Heart of Midlothian | 2:0 | ||||
| 5. Round | 12/09/2004 | Heart of Midlothian | - | Rangers FC | 0:0 | ||||
| 6. Round | 19/09/2004 | Dunfermline Athletic | - | Heart of Midlothian | 1:0 | ||||
| 7. Round | 25/09/2004 | Heart of Midlothian | - | Inverness CT | 1:0 | ||||
| 8. Round | 03/10/2004 | Heart of Midlothian | - | Livingston FC | 0:0 | ||||
| 9. Round | 16/10/2004 | Celtic FC | - | Heart of Midlothian | 3:0 | ||||
| 10. Round | 24/10/2004 | Heart of Midlothian | - | Hibernian FC | 2:1 | ||||
| 13. Round | 07/11/2004 | Aberdeen FC | - | Heart of Midlothian | 0:1 | |
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| 17. Round | 04/12/2004 | Heart of Midlothian | - | Dunfermline Athletic | 3:0 | ||||
| 20. Round | 26/12/2004 | Heart of Midlothian | - | Celtic FC | 0:2 | ||||
| 21. Round | 02/01/2005 | Hibernian FC | - | Heart of Midlothian | 1:1 | |
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| 22. Round | 15/01/2005 | Heart of Midlothian | - | Dundee United | 3:2 | ||||
| 23. Round | 22/01/2005 | Dundee FC | - | Heart of Midlothian | 1:1 | |
England