| 1. Round | 31/07/1998 | Kilmarnock FC | - | Dundee United | 2:0 | ||||
| 2. Round | 14/08/1998 | St. Johnstone FC | - | Kilmarnock FC | 0:0 | ||||
| 3. Round | 21/08/1998 | Kilmarnock FC | - | Rangers FC | 1:3 |  |
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| 24. Round | 05/03/1999 | Kilmarnock FC | - | Dunfermline Athletic | 0:0 | ||||
| 27. Round | 12/03/1999 | St. Johnstone FC | - | Kilmarnock FC | 0:1 |  |
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| 28. Round | 20/03/1999 | Kilmarnock FC | - | Celtic FC | 0:0 | ||||
| 29. Round | 02/04/1999 | Heart of Midlothian | - | Kilmarnock FC | 2:2 | ||||
| 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 | |
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| 33. Round | 30/04/1999 | Kilmarnock FC | - | Motherwell FC | 0:1 | ||||
| 34. Round | 07/05/1999 | Dundee United | - | Kilmarnock FC | 0:0 | ||||
| 35. Round | 14/05/1999 | Kilmarnock FC | - | St. Johnstone FC | 1:1 | |
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| 36. Round | 22/05/1999 | Rangers FC | - | Kilmarnock FC | 1:1 |
Scotland