| 3. Ronde | 22.08.1998 | Heart of Midlothian | - | Aberdeen FC | 2:0 | ||||
| 4. Ronde | 30.08.1998 | Kilmarnock FC | - | Heart of Midlothian | 3:0 | ||||
| 11. Ronde | 24.10.1998 | Heart of Midlothian | - | Dundee United | 0:1 | ||||
| 12. Ronde | 31.10.1998 | Dundee FC | - | Heart of Midlothian | 1:0 |  |
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| 18. Ronde | 12.12.1998 | Aberdeen FC | - | Heart of Midlothian | 2:0 | ||||
| 19. Ronde | 19.12.1998 | Heart of Midlothian | - | Rangers FC | 2:3 | |
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| 20. Ronde | 26.12.1998 | Kilmarnock FC | - | Heart of Midlothian | 1:0 | ||||
| 26. Ronde | 30.12.1998 | Heart of Midlothian | - | Dundee FC | 1:2 | |
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| 21. Ronde | 02.01.1999 | Dunfermline Athletic | - | Heart of Midlothian | 0:0 | ||||
| 29. Ronde | 03.04.1999 | Heart of Midlothian | - | Kilmarnock FC | 2:2 | ||||
| 27. Ronde | 06.04.1999 | Dundee United | - | Heart of Midlothian | 1:3 | ||||
| 30. Ronde | 14.04.1999 | Heart of Midlothian | - | Celtic FC | 2:4 | ||||
| 31. Ronde | 17.04.1999 | St. Johnstone FC | - | Heart of Midlothian | 0:0 | ||||
| 32. Ronde | 24.04.1999 | Motherwell FC | - | Heart of Midlothian | 0:4 | ||||
| 33. Ronde | 03.05.1999 | Heart of Midlothian | - | Dunfermline Athletic | 2:0 |
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