| 1. Jornada | 01.08.1998 | Kilmarnock FC | - | Dundee United | 2:0 |  |
|||
| 2. Jornada | 16.08.1998 | Dundee United | - | Heart of Midlothian | 0:0 | ||||
| 4. Jornada | 30.08.1998 | Motherwell FC | - | Dundee United | 1:0 | ||||
| 12. Jornada | 31.10.1998 | Rangers FC | - | Dundee United | 2:1 | |
|||
| 13. Jornada | 07.11.1998 | Dundee United | - | Motherwell FC | 2:2 |  |
|||
| 14. Jornada | 15.11.1998 | Dunfermline Athletic | - | Dundee United | 2:1 | ||||
| 15. Jornada | 22.11.1998 | Dundee United | - | Dundee FC | 0:1 | ||||
| 22. Jornada | 30.01.1999 | Dundee United | - | Dunfermline Athletic | 1:1 | |
|||
| 23. Jornada | 06.02.1999 | St. Johnstone FC | - | Dundee United | 1:0 | ||||
| 24. Jornada | 20.02.1999 | Dundee United | - | Aberdeen FC | 3:0 | ||||
| 28. Jornada | 20.03.1999 | Rangers FC | - | Dundee United | 0:1 | ||||
| 27. Jornada | 06.04.1999 | Dundee United | - | Heart of Midlothian | 1:3 | ||||
| 31. Jornada | 17.04.1999 | Aberdeen FC | - | Dundee United | 0:4 | ||||
| 32. Jornada | 24.04.1999 | Dunfermline Athletic | - | Dundee United | 2:2 |
Islandia