| 1. Round | 15/08/2009 | Kilmarnock FC | - | Hamilton Academical | 3:0 | ||||
| 2. Round | 22/08/2009 | Motherwell FC | - | Kilmarnock FC | 3:1 | ||||
| 10. Round | 31/10/2009 | Celtic FC | - | Kilmarnock FC | 3:0 | ||||
| 20. Round | 16/01/2010 | Kilmarnock FC | - | Motherwell FC | 0:3 | ||||
| 21. Round | 23/01/2010 | Aberdeen FC | - | Kilmarnock FC | 1:0 | ||||
| 22. Round | 26/01/2010 | Hamilton Academical | - | Kilmarnock FC | 0:0 | ||||
| 23. Round | 30/01/2010 | Kilmarnock FC | - | Dundee United | 4:4 | ||||
| 18. Round | 02/02/2010 | Kilmarnock FC | - | Celtic FC | 1:0 | ||||
| 24. Round | 10/02/2010 | Falkirk FC | - | Kilmarnock FC | 0:1 | ||||
| 25. Round | 13/02/2010 | Kilmarnock FC | - | St. Johnstone FC | 3:2 | ||||
| 26. Round | 20/02/2010 | Kilmarnock FC | - | St. Mirren FC | 1:1 | ||||
| 27. Round | 27/02/2010 | Motherwell FC | - | Kilmarnock FC | 1:0 | ||||
| 28. Round | 06/03/2010 | Hibernian FC | - | Kilmarnock FC | 1:0 | ||||
| 29. Round | 09/03/2010 | Kilmarnock FC | - | Rangers FC | 0:2 | ||||
| 30. Round | 24/03/2010 | Kilmarnock FC | - | Hamilton Academical | 1:2 | ||||
| 31. Round | 27/03/2010 | Celtic FC | - | Kilmarnock FC | 3:1 | ||||
| 32. Round | 04/04/2010 | Kilmarnock FC | - | Aberdeen FC | 2:0 | ||||
| 33. Round | 10/04/2010 | Heart of Midlothian | - | Kilmarnock FC | 1:0 |
Scotland