| 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 | ||||
| 11. Ronde | 24.10.1998 | Heart of Midlothian | - | Dundee United | 0:1 | ||||
| 13. Ronde | 07.11.1998 | Heart of Midlothian | - | Kilmarnock FC | 2:1 | ||||
| 14. Ronde | 14.11.1998 | Motherwell FC | - | Heart of Midlothian | 3:2 | ||||
| 15. Ronde | 21.11.1998 | Heart of Midlothian | - | Dunfermline Athletic | 2:1 | ||||
| 17. Ronde | 06.12.1998 | Heart of Midlothian | - | Celtic FC | 2:1 | ||||
| 16. Ronde | 09.12.1998 | St. Johnstone FC | - | Heart of Midlothian | 1:1 | ||||
| 19. Ronde | 19.12.1998 | Heart of Midlothian | - | Rangers FC | 2:3 | ||||
| 26. Ronde | 30.12.1998 | Heart of Midlothian | - | Dundee FC | 1:2 | ||||
| 35. Ronde | 15.05.1999 | Heart of Midlothian | - | Dundee United | 4:1 | ||||
| 36. Ronde | 23.05.1999 | Aberdeen FC | - | Heart of Midlothian | 2:5 |
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