| 10. Jornada | 17.10.1998 | Dundee United | - | Kilmarnock FC | 0:2 | ||||
| 11. Jornada | 24.10.1998 | Kilmarnock FC | - | St. Johnstone FC | 2:2 | ||||
| 12. Jornada | 31.10.1998 | Kilmarnock FC | - | Celtic FC | 2:0 | ||||
| 19. Jornada | 20.12.1998 | Kilmarnock FC | - | Dundee United | 2:0 | ||||
| 22. Jornada | 30.01.1999 | Kilmarnock FC | - | Dundee FC | 0:0 | ||||
| 23. Jornada | 06.02.1999 | Aberdeen FC | - | Kilmarnock FC | 2:1 | ||||
| 30. Jornada | 10.04.1999 | Kilmarnock FC | - | Aberdeen FC | 4:2 |  |
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| 31. Jornada | 17.04.1999 | Dunfermline Athletic | - | Kilmarnock FC | 0:6 | ||||
| 32. Jornada | 24.04.1999 | Dundee FC | - | Kilmarnock FC | 2:1 | ||||
| 33. Jornada | 01.05.1999 | Kilmarnock FC | - | Motherwell FC | 0:1 | ||||
| 35. Jornada | 15.05.1999 | Kilmarnock FC | - | St. Johnstone FC | 1:1 | ||||
| 36. Jornada | 23.05.1999 | Rangers FC | - | Kilmarnock FC | 1:1 |
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