| 9. Round | 03/10/1998 | Heart of Midlothian | - | St. Johnstone FC | 1:1 | ||||
| 10. Round | 16/10/1998 | Rangers FC | - | Heart of Midlothian | 3:0 | ||||
| 11. Round | 23/10/1998 | Heart of Midlothian | - | Dundee United | 0:1 | ||||
| 13. Round | 06/11/1998 | Heart of Midlothian | - | Kilmarnock FC | 2:1 | ||||
| 14. Round | 13/11/1998 | Motherwell FC | - | Heart of Midlothian | 3:2 | ||||
| 15. Round | 20/11/1998 | Heart of Midlothian | - | Dunfermline Athletic | 2:1 | ||||
| 17. Round | 05/12/1998 | Heart of Midlothian | - | Celtic FC | 2:1 | ||||
| 16. Round | 08/12/1998 | St. Johnstone FC | - | Heart of Midlothian | 1:1 | ||||
| 19. Round | 18/12/1998 | Heart of Midlothian | - | Rangers FC | 2:3 | ||||
| 26. Round | 29/12/1998 | Heart of Midlothian | - | Dundee FC | 1:2 | ||||
| 35. Round | 14/05/1999 | Heart of Midlothian | - | Dundee United | 4:1 | ||||
| 36. Round | 22/05/1999 | Aberdeen FC | - | Heart of Midlothian | 2:5 |
Spain