| 2. Round | 15/08/1998 | Dundee United | - | Heart of Midlothian | 0:0 | ||||
| 3. Round | 21/08/1998 | Celtic FC | - | Dundee United | 2:1 | ||||
| 4. Round | 29/08/1998 | Motherwell FC | - | Dundee United | 1:0 | ||||
| 8. Round | 25/09/1998 | St. Johnstone FC | - | Dundee United | 1:3 | ||||
| 9. Round | 03/10/1998 | Dundee United | - | Aberdeen FC | 1:0 | ||||
| 12. Round | 30/10/1998 | Rangers FC | - | Dundee United | 2:1 |  |
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| 13. Round | 06/11/1998 | Dundee United | - | Motherwell FC | 2:2 | ||||
| 14. Round | 14/11/1998 | Dunfermline Athletic | - | Dundee United | 2:1 | ||||
| 15. Round | 21/11/1998 | Dundee United | - | Dundee FC | 0:1 | ||||
| 16. Round | 27/11/1998 | Aberdeen FC | - | Dundee United | 0:3 | ||||
| 17. Round | 04/12/1998 | Dundee United | - | St. Johnstone FC | 1:1 | ||||
| 18. Round | 11/12/1998 | Dundee United | - | Celtic FC | 1:1 | ||||
| 19. Round | 19/12/1998 | Kilmarnock FC | - | Dundee United | 2:0 | ||||
| 20. Round | 25/12/1998 | Motherwell FC | - | Dundee United | 2:0 | ||||
| 26. Round | 29/12/1998 | Dundee United | - | Rangers FC | 1:2 | ||||
| 21. Round | 01/01/1999 | Dundee FC | - | Dundee United | 1:3 |
France