| 24. Ronde | 20.02.1999 | Heart of Midlothian | - | St. Johnstone FC | 0:2 | ||||
| 25. Ronde | 27.02.1999 | Heart of Midlothian | - | Aberdeen FC | 0:2 | ||||
| 29. Ronde | 03.04.1999 | Heart of Midlothian | - | Kilmarnock FC | 2:2 |  |
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| 27. Ronde | 06.04.1999 | Dundee United | - | Heart of Midlothian | 1:3 |  |
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| 30. Ronde | 14.04.1999 | Heart of Midlothian | - | Celtic FC | 2:4 | |
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| 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 | |
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| 33. Ronde | 03.05.1999 | Heart of Midlothian | - | Dunfermline Athletic | 2:0 | |
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| 34. Ronde | 09.05.1999 | Rangers FC | - | Heart of Midlothian | 0:0 | ||||
| 35. Ronde | 15.05.1999 | Heart of Midlothian | - | Dundee United | 4:1 | |
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| 36. Ronde | 23.05.1999 | Aberdeen FC | - | Heart of Midlothian | 2:5 | |
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