| 1. Round | 09/08/2003 | Heart of Midlothian | - | Aberdeen FC | 2:0 | ||||
| 2. Round | 17/08/2003 | Hibernian FC | - | Heart of Midlothian | 1:0 | ||||
| 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 | ||||
| 8. Round | 04/10/2003 | Heart of Midlothian | - | Dundee FC | 2:2 | ||||
| 9. Round | 18/10/2003 | Celtic FC | - | Heart of Midlothian | 5:0 |
Finland