| 2. Jornada | 15.08.1998 | Dunfermline Athletic | - | Dundee FC | 2:0 | ||||
| 3. Jornada | 23.08.1998 | Dundee FC | - | St. Johnstone FC | 0:1 | ||||
| 4. Jornada | 29.08.1998 | Dundee FC | - | Celtic FC | 1:1 | ||||
| 6. Jornada | 19.09.1998 | Dundee FC | - | Dundee United | 2:2 | ||||
| 10. Jornada | 17.10.1998 | Aberdeen FC | - | Dundee FC | 2:2 | ||||
| 11. Jornada | 28.10.1998 | Dundee FC | - | Dunfermline Athletic | 1:0 | ||||
| 12. Jornada | 31.10.1998 | Dundee FC | - | Heart of Midlothian | 1:0 | ||||
| 13. Jornada | 07.11.1998 | Celtic FC | - | Dundee FC | 6:1 |  |
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| 14. Jornada | 14.11.1998 | Dundee FC | - | Kilmarnock FC | 1:1 | ||||
| 15. Jornada | 22.11.1998 | Dundee United | - | Dundee FC | 0:1 | |
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| 18. Jornada | 12.12.1998 | St. Johnstone FC | - | Dundee FC | 1:1 | ||||
| 19. Jornada | 19.12.1998 | Dundee FC | - | Aberdeen FC | 1:2 | ||||
| 20. Jornada | 27.12.1998 | Dundee FC | - | Celtic FC | 0:3 | ||||
| 21. Jornada | 02.01.1999 | Dundee FC | - | Dundee United | 1:3 | ||||
| 29. Jornada | 03.04.1999 | Celtic FC | - | Dundee FC | 5:0 |
Escocia