| 1. Ronde | 31.07.1999 | Rangers FC | - | Kilmarnock FC | 2:1 | ||||
| 2. Ronde | 07.08.1999 | Kilmarnock FC | - | Aberdeen FC | 2:0 | ||||
| 3. Ronde | 15.08.1999 | St. Johnstone FC | - | Kilmarnock FC | 2:0 | ||||
| 6. Ronde | 12.09.1999 | Kilmarnock FC | - | Celtic FC | 0:1 | ||||
| 7. Ronde | 19.09.1999 | Hibernian FC | - | Kilmarnock FC | 0:3 | ||||
| 8. Ronde | 25.09.1999 | Kilmarnock FC | - | Dundee FC | 0:2 |  |
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| 14. Ronde | 20.11.1999 | Kilmarnock FC | - | Dundee United | 1:1 | ||||
| 19. Ronde | 18.12.1999 | Kilmarnock FC | - | St. Johnstone FC | 1:2 | ||||
| 36. Ronde | 21.05.2000 | Kilmarnock FC | - | St. Johnstone FC | 3:2 |
Schotland