| 4. Ronde | 30.08.1998 | Kilmarnock FC | - | Heart of Midlothian | 3:0 | ||||
| 5. Ronde | 12.09.1998 | Heart of Midlothian | - | Dundee FC | 0:2 | ||||
| 6. Ronde | 20.09.1998 | Dunfermline Athletic | - | Heart of Midlothian | 1:1 | ||||
| 7. Ronde | 23.09.1998 | Heart of Midlothian | - | Motherwell FC | 3:0 | ||||
| 8. Ronde | 26.09.1998 | Celtic FC | - | Heart of Midlothian | 1:1 | ||||
| 9. Ronde | 04.10.1998 | Heart of Midlothian | - | St. Johnstone FC | 1:1 |  |
|||
| 10. Ronde | 17.10.1998 | Rangers FC | - | Heart of Midlothian | 3:0 | ||||
| 19. Ronde | 19.12.1998 | Heart of Midlothian | - | Rangers FC | 2:3 | ||||
| 20. Ronde | 26.12.1998 | Kilmarnock FC | - | Heart of Midlothian | 1:0 | ||||
| 26. Ronde | 30.12.1998 | Heart of Midlothian | - | Dundee FC | 1:2 | ||||
| 22. Ronde | 30.01.1999 | Heart of Midlothian | - | Motherwell FC | 0:2 | ||||
| 29. Ronde | 03.04.1999 | Heart of Midlothian | - | Kilmarnock FC | 2:2 |  |
|||
| 36. Ronde | 23.05.1999 | Aberdeen FC | - | Heart of Midlothian | 2:5 |
Engeland