| 1. Ronde | 01.08.1998 | Kilmarnock FC | - | Dundee United | 2:0 | ||||
| 2. Ronde | 16.08.1998 | Dundee United | - | Heart of Midlothian | 0:0 |  |
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| 3. Ronde | 22.08.1998 | Celtic FC | - | Dundee United | 2:1 | ||||
| 6. Ronde | 19.09.1998 | Dundee FC | - | Dundee United | 2:2 | ||||
| 10. Ronde | 17.10.1998 | Dundee United | - | Kilmarnock FC | 0:2 | ||||
| 12. Ronde | 31.10.1998 | Rangers FC | - | Dundee United | 2:1 | ||||
| 14. Ronde | 15.11.1998 | Dunfermline Athletic | - | Dundee United | 2:1 | ||||
| 17. Ronde | 05.12.1998 | Dundee United | - | St. Johnstone FC | 1:1 | ||||
| 19. Ronde | 20.12.1998 | Kilmarnock FC | - | Dundee United | 2:0 | ||||
| 21. Ronde | 02.01.1999 | Dundee FC | - | Dundee United | 1:3 |  |
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| 22. Ronde | 30.01.1999 | Dundee United | - | Dunfermline Athletic | 1:1 | ||||
| 23. Ronde | 06.02.1999 | St. Johnstone FC | - | Dundee United | 1:0 | ||||
| 34. Ronde | 08.05.1999 | Dundee United | - | Kilmarnock FC | 0:0 | ||||
| 35. Ronde | 15.05.1999 | Heart of Midlothian | - | Dundee United | 4:1 | ||||
| 36. Ronde | 23.05.1999 | Dundee United | - | Celtic FC | 1:2 |
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