| 3. Round | 21/08/1998 | Kilmarnock FC | - | Rangers FC | 1:3 | ||||
| 4. Round | 29/08/1998 | Kilmarnock FC | - | Heart of Midlothian | 3:0 | ||||
| 5. Round | 11/09/1998 | Celtic FC | - | Kilmarnock FC | 1:1 | ||||
| 6. Round | 18/09/1998 | Motherwell FC | - | Kilmarnock FC | 0:0 |  |
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| 7. Round | 22/09/1998 | Kilmarnock FC | - | Dundee FC | 2:1 | ||||
| 8. Round | 26/09/1998 | Aberdeen FC | - | Kilmarnock FC | 0:1 | ||||
| 9. Round | 02/10/1998 | Kilmarnock FC | - | Dunfermline Athletic | 0:0 | ||||
| 24. Round | 05/03/1999 | Kilmarnock FC | - | Dunfermline Athletic | 0:0 | ||||
| 27. Round | 12/03/1999 | St. Johnstone FC | - | Kilmarnock FC | 0:1 | ||||
| 28. Round | 20/03/1999 | Kilmarnock FC | - | Celtic FC | 0:0 | ||||
| 29. Round | 02/04/1999 | Heart of Midlothian | - | Kilmarnock FC | 2:2 | |
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| 30. Round | 09/04/1999 | Kilmarnock FC | - | Aberdeen FC | 4:2 | ||||
| 31. Round | 16/04/1999 | Dunfermline Athletic | - | Kilmarnock FC | 0:6 | ||||
| 32. Round | 23/04/1999 | Dundee FC | - | Kilmarnock FC | 2:1 | ||||
| 35. Round | 14/05/1999 | Kilmarnock FC | - | St. Johnstone FC | 1:1 | ||||
| 36. Round | 22/05/1999 | Rangers FC | - | Kilmarnock FC | 1:1 |
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