| 1. Ronde | 01.08.1998 | Dundee FC | - | Aberdeen FC | 0:2 | ||||
| 2. Ronde | 15.08.1998 | Dunfermline Athletic | - | Dundee FC | 2:0 |  |
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| 3. Ronde | 23.08.1998 | Dundee FC | - | St. Johnstone FC | 0:1 | ||||
| 8. Ronde | 26.09.1998 | Dundee FC | - | Motherwell FC | 1:0 | ||||
| 9. Ronde | 04.10.1998 | Rangers FC | - | Dundee FC | 1:0 | ||||
| 12. Ronde | 31.10.1998 | Dundee FC | - | Heart of Midlothian | 1:0 | ||||
| 14. Ronde | 14.11.1998 | Dundee FC | - | Kilmarnock FC | 1:1 | ||||
| 15. Ronde | 22.11.1998 | Dundee United | - | Dundee FC | 0:1 | ||||
| 17. Ronde | 16.12.1998 | Motherwell FC | - | Dundee FC | 2:1 | ||||
| 21. Ronde | 02.01.1999 | Dundee FC | - | Dundee United | 1:3 | ||||
| 23. Ronde | 06.02.1999 | Dundee FC | - | Motherwell FC | 1:0 | ||||
| 24. Ronde | 20.02.1999 | Rangers FC | - | Dundee FC | 6:1 | ||||
| 25. Ronde | 27.02.1999 | Dundee FC | - | St. Johnstone FC | 0:1 | ||||
| 31. Ronde | 18.04.1999 | Dundee FC | - | Rangers FC | 1:1 | ||||
| 34. Ronde | 08.05.1999 | Aberdeen FC | - | Dundee FC | 1:2 | ||||
| 35. Ronde | 15.05.1999 | Dundee FC | - | Dunfermline Athletic | 3:1 |
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