| 24. Round | 19/02/1999 | Heart of Midlothian | - | St. Johnstone FC | 0:2 | ||||
| 25. Round | 26/02/1999 | Heart of Midlothian | - | Aberdeen FC | 0:2 | ||||
| 29. Round | 02/04/1999 | Heart of Midlothian | - | Kilmarnock FC | 2:2 |  |
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| 27. Round | 05/04/1999 | Dundee United | - | Heart of Midlothian | 1:3 |  |
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| 30. Round | 13/04/1999 | Heart of Midlothian | - | Celtic FC | 2:4 | |
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| 31. Round | 16/04/1999 | St. Johnstone FC | - | Heart of Midlothian | 0:0 | ||||
| 32. Round | 23/04/1999 | Motherwell FC | - | Heart of Midlothian | 0:4 | |
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| 33. Round | 02/05/1999 | Heart of Midlothian | - | Dunfermline Athletic | 2:0 | |
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| 34. Round | 08/05/1999 | Rangers FC | - | Heart of Midlothian | 0:0 | ||||
| 35. Round | 14/05/1999 | Heart of Midlothian | - | Dundee United | 4:1 | |
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| 36. Round | 22/05/1999 | Aberdeen FC | - | Heart of Midlothian | 2:5 | |
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Scotland