| 1. Round | 31/07/1998 | Kilmarnock FC | - | Dundee United | 2:0 |  |
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| 2. Round | 15/08/1998 | Dundee United | - | Heart of Midlothian | 0:0 | ||||
| 4. Round | 29/08/1998 | Motherwell FC | - | Dundee United | 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 |  |
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| 14. Round | 14/11/1998 | Dunfermline Athletic | - | Dundee United | 2:1 | ||||
| 15. Round | 21/11/1998 | Dundee United | - | Dundee FC | 0:1 | ||||
| 22. Round | 29/01/1999 | Dundee United | - | Dunfermline Athletic | 1:1 | |
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| 23. Round | 05/02/1999 | St. Johnstone FC | - | Dundee United | 1:0 | ||||
| 24. Round | 19/02/1999 | Dundee United | - | Aberdeen FC | 3:0 | ||||
| 28. Round | 19/03/1999 | Rangers FC | - | Dundee United | 0:1 | ||||
| 27. Round | 05/04/1999 | Dundee United | - | Heart of Midlothian | 1:3 | ||||
| 31. Round | 16/04/1999 | Aberdeen FC | - | Dundee United | 0:4 | ||||
| 32. Round | 23/04/1999 | Dunfermline Athletic | - | Dundee United | 2:2 |
Iceland