| 3. Round | 23/08/2003 | Heart of Midlothian | - | Dundee United | 3:0 | ||||
| 4. Round | 31/08/2003 | Dunfermline Athletic | - | Heart of Midlothian | 0:1 | ||||
| 5. Round | 13/09/2003 | Kilmarnock FC | - | Heart of Midlothian | 0:2 | ||||
| 6. Round | 21/09/2003 | Heart of Midlothian | - | Rangers FC | 0:4 | ||||
| 7. Round | 27/09/2003 | Motherwell FC | - | Heart of Midlothian | 1:1 | ||||
| 13. Round | 23/11/2003 | Heart of Midlothian | - | Hibernian FC | 2:0 | ||||
| 21. Round | 24/01/2004 | Heart of Midlothian | - | Partick Thistle | 2:0 | ||||
| 23. Round | 11/02/2004 | Heart of Midlothian | - | Aberdeen FC | 1:0 | ||||
| 27. Round | 07/03/2004 | Kilmarnock FC | - | Heart of Midlothian | 1:1 | ||||
| 28. Round | 13/03/2004 | Heart of Midlothian | - | Rangers FC | 1:1 | ||||
| 30. Round | 27/03/2004 | Heart of Midlothian | - | Dundee FC | 3:1 |  |
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| 32. Round | 10/04/2004 | Partick Thistle | - | Heart of Midlothian | 1:0 | ||||
| 33. Round | 17/04/2004 | Heart of Midlothian | - | Livingston FC | 1:1 |
Scotland