| 1. Ronde | 01.08.1998 | Kilmarnock FC | - | Dundee United | 2:0 |  |
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| 2. Ronde | 16.08.1998 | Dundee United | - | Heart of Midlothian | 0:0 | ||||
| 4. Ronde | 30.08.1998 | Motherwell FC | - | Dundee United | 1:0 | ||||
| 12. Ronde | 31.10.1998 | Rangers FC | - | Dundee United | 2:1 | |
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| 13. Ronde | 07.11.1998 | Dundee United | - | Motherwell FC | 2:2 |  |
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| 14. Ronde | 15.11.1998 | Dunfermline Athletic | - | Dundee United | 2:1 | ||||
| 15. Ronde | 22.11.1998 | Dundee United | - | Dundee FC | 0:1 | ||||
| 22. Ronde | 30.01.1999 | Dundee United | - | Dunfermline Athletic | 1:1 | |
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| 23. Ronde | 06.02.1999 | St. Johnstone FC | - | Dundee United | 1:0 | ||||
| 24. Ronde | 20.02.1999 | Dundee United | - | Aberdeen FC | 3:0 | ||||
| 28. Ronde | 20.03.1999 | Rangers FC | - | Dundee United | 0:1 | ||||
| 27. Ronde | 06.04.1999 | Dundee United | - | Heart of Midlothian | 1:3 | ||||
| 31. Ronde | 17.04.1999 | Aberdeen FC | - | Dundee United | 0:4 | ||||
| 32. Ronde | 24.04.1999 | Dunfermline Athletic | - | Dundee United | 2:2 |
IJsland