| 5. Ronde | 12.09.1998 | Heart of Midlothian | - | Dundee FC | 0:2 | ||||
| 7. Ronde | 23.09.1998 | Kilmarnock FC | - | Dundee FC | 2:1 | ||||
| 14. Ronde | 14.11.1998 | Dundee FC | - | Kilmarnock FC | 1:1 | ||||
| 15. Ronde | 22.11.1998 | Dundee United | - | Dundee FC | 0:1 | ||||
| 18. Ronde | 12.12.1998 | St. Johnstone FC | - | Dundee FC | 1:1 |  |
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| 17. Ronde | 16.12.1998 | Motherwell FC | - | Dundee FC | 2:1 | ||||
| 20. Ronde | 27.12.1998 | Dundee FC | - | Celtic FC | 0:3 | |
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| 22. Ronde | 30.01.1999 | Kilmarnock FC | - | Dundee FC | 0:0 | ||||
| 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 |
Engeland