| 1. Round | 30/07/2005 | Kilmarnock FC | - | Heart of Midlothian | 2:4 |  |
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| 2. Round | 06/08/2005 | Aberdeen FC | - | Kilmarnock FC | 1:2 | ||||
| 3. Round | 13/08/2005 | Kilmarnock FC | - | Motherwell FC | 4:1 | ||||
| 4. Round | 20/08/2005 | Inverness CT | - | Kilmarnock FC | 2:2 | ||||
| 5. Round | 27/08/2005 | Kilmarnock FC | - | Livingston FC | 3:0 | ||||
| 9. Round | 01/10/2005 | Dundee United | - | Kilmarnock FC | 0:0 | |
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| 10. Round | 15/10/2005 | Hibernian FC | - | Kilmarnock FC | 4:2 | ||||
| 11. Round | 23/10/2005 | Kilmarnock FC | - | Celtic FC | 0:1 | |
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| 24. Round | 28/01/2006 | Aberdeen FC | - | Kilmarnock FC | 2:2 | ||||
| 25. Round | 08/02/2006 | Kilmarnock FC | - | Motherwell FC | 2:0 | ||||
| 26. Round | 11/02/2006 | Inverness CT | - | Kilmarnock FC | 3:3 | ||||
| 27. Round | 18/02/2006 | Kilmarnock FC | - | Livingston FC | 3:1 | ||||
| 28. Round | 04/03/2006 | Kilmarnock FC | - | Dunfermline Athletic | 1:0 |
Scotland
