| 3. Round | 21/08/1998 | Heart of Midlothian | - | Aberdeen FC | 2:0 | ||||
| 4. Round | 29/08/1998 | Kilmarnock FC | - | Heart of Midlothian | 3:0 | ||||
| 5. Round | 11/09/1998 | Heart of Midlothian | - | Dundee FC | 0:2 | ||||
| 9. Round | 03/10/1998 | Heart of Midlothian | - | St. Johnstone FC | 1:1 | ||||
| 11. Round | 23/10/1998 | Heart of Midlothian | - | Dundee United | 0:1 |  |
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| 12. Round | 30/10/1998 | Dundee FC | - | Heart of Midlothian | 1:0 | ||||
| 13. Round | 06/11/1998 | Heart of Midlothian | - | Kilmarnock FC | 2:1 | ||||
| 14. Round | 13/11/1998 | Motherwell FC | - | Heart of Midlothian | 3:2 | ||||
| 19. Round | 18/12/1998 | Heart of Midlothian | - | Rangers FC | 2:3 | ||||
| 20. Round | 25/12/1998 | Kilmarnock FC | - | Heart of Midlothian | 1:0 | ||||
| 23. Round | 05/02/1999 | Celtic FC | - | Heart of Midlothian | 3:0 | ||||
| 24. Round | 19/02/1999 | Heart of Midlothian | - | St. Johnstone FC | 0:2 |
Angola