| 1. Ronde | 02.08.1998 | Heart of Midlothian | - | Rangers FC | 2:1 | ||||
| 2. Ronde | 16.08.1998 | Dundee United | - | Heart of Midlothian | 0:0 | ||||
| 6. Ronde | 20.09.1998 | Dunfermline Athletic | - | Heart of Midlothian | 1:1 | ||||
| 7. Ronde | 23.09.1998 | Heart of Midlothian | - | Motherwell FC | 3:0 |  |
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| 8. Ronde | 26.09.1998 | Celtic FC | - | Heart of Midlothian | 1:1 | |
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| 9. Ronde | 04.10.1998 | Heart of Midlothian | - | St. Johnstone FC | 1:1 | |
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| 10. Ronde | 17.10.1998 | Rangers FC | - | Heart of Midlothian | 3:0 | ||||
| 11. Ronde | 24.10.1998 | Heart of Midlothian | - | Dundee United | 0:1 | ||||
| 22. Ronde | 30.01.1999 | Heart of Midlothian | - | Motherwell FC | 0:2 | |
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| 23. Ronde | 06.02.1999 | Celtic FC | - | Heart of Midlothian | 3:0 | ||||
| 25. Ronde | 27.02.1999 | Heart of Midlothian | - | Aberdeen FC | 0:2 |
Italië