| 1. Round | 01/08/1998 | Heart of Midlothian | - | Rangers FC | 2:1 | ||||
| 2. Round | 15/08/1998 | Dundee United | - | Heart of Midlothian | 0:0 | ||||
| 4. Round | 29/08/1998 | Kilmarnock FC | - | Heart of Midlothian | 3:0 | ||||
| 5. Round | 11/09/1998 | Heart of Midlothian | - | Dundee FC | 0:2 | ||||
| 6. Round | 19/09/1998 | Dunfermline Athletic | - | Heart of Midlothian | 1:1 | ||||
| 7. Round | 22/09/1998 | Heart of Midlothian | - | Motherwell FC | 3:0 |  |
|||
| 8. Round | 25/09/1998 | Celtic FC | - | Heart of Midlothian | 1:1 | ||||
| 15. Round | 20/11/1998 | Heart of Midlothian | - | Dunfermline Athletic | 2:1 | |
Scotland