| 3. Ronde | 22.08.1998 | Heart of Midlothian | - | Aberdeen FC | 2:0 | ||||
| 4. Ronde | 30.08.1998 | Kilmarnock FC | - | Heart of Midlothian | 3:0 | ||||
| 5. Ronde | 12.09.1998 | Heart of Midlothian | - | Dundee FC | 0:2 | ||||
| 9. Ronde | 04.10.1998 | Heart of Midlothian | - | St. Johnstone FC | 1:1 | ||||
| 11. Ronde | 24.10.1998 | Heart of Midlothian | - | Dundee United | 0:1 |  |
|||
| 12. Ronde | 31.10.1998 | Dundee FC | - | Heart of Midlothian | 1:0 | ||||
| 13. Ronde | 07.11.1998 | Heart of Midlothian | - | Kilmarnock FC | 2:1 | ||||
| 14. Ronde | 14.11.1998 | Motherwell FC | - | Heart of Midlothian | 3:2 | ||||
| 19. Ronde | 19.12.1998 | Heart of Midlothian | - | Rangers FC | 2:3 | ||||
| 20. Ronde | 26.12.1998 | Kilmarnock FC | - | Heart of Midlothian | 1:0 | ||||
| 23. Ronde | 06.02.1999 | Celtic FC | - | Heart of Midlothian | 3:0 | ||||
| 24. Ronde | 20.02.1999 | Heart of Midlothian | - | St. Johnstone FC | 0:2 |
Angola