| 7. Round | 22/09/1998 | Dundee United | - | Dunfermline Athletic | 1:1 | ||||
| 9. Round | 03/10/1998 | Dundee United | - | Aberdeen FC | 1:0 | ||||
| 10. Round | 16/10/1998 | Dundee United | - | Kilmarnock FC | 0:2 | ||||
| 11. Round | 23/10/1998 | Heart of Midlothian | - | Dundee United | 0:1 | ||||
| 12. Round | 30/10/1998 | Rangers FC | - | 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 | ||||
| 19. Round | 19/12/1998 | Kilmarnock FC | - | Dundee United | 2:0 | ||||
| 22. Round | 29/01/1999 | Dundee United | - | Dunfermline Athletic | 1:1 | ||||
| 25. Round | 26/02/1999 | Celtic FC | - | Dundee United | 2:1 |
Scotland