| 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 |  |
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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 | ||||
| 34. Ronde | 09.05.1999 | Rangers FC | - | Heart of Midlothian | 0:0 | |
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| 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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