| 6. Round | 18/09/2021 | Partick Thistle | - | Kilmarnock FC | 0:2 | ||||
| 10. Round | 23/10/2021 | Kilmarnock FC | - | Hamilton Academical | 2:1 | ||||
| 11. Round | 26/10/2021 | Ayr United | - | Kilmarnock FC | 0:1 | ||||
| 12. Round | 30/10/2021 | Kilmarnock FC | - | Queen Of The South | 4:0 | ||||
| 13. Round | 06/11/2021 | Kilmarnock FC | - | Partick Thistle | 0:1 |  |
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| 14. Round | 13/11/2021 | Greenock Morton FC | - | Kilmarnock FC | 0:2 | ||||
| 15. Round | 20/11/2021 | Kilmarnock FC | - | Arbroath FC | 0:1 | ||||
| 16. Round | 03/12/2021 | Inverness CT | - | Kilmarnock FC | 1:0 | ||||
| 18. Round | 12/02/2022 | Kilmarnock FC | - | Dunfermline Athletic | 2:1 | ||||
| 26. Round | 19/02/2022 | Kilmarnock FC | - | Raith Rovers | 3:0 | ||||
| 27. Round | 26/02/2022 | Dunfermline Athletic | - | Kilmarnock FC | 0:0 | ||||
| 28. Round | 05/03/2022 | Kilmarnock FC | - | Hamilton Academical | 2:0 | ||||
| 29. Round | 11/03/2022 | Ayr United | - | Kilmarnock FC | 1:3 | ||||
| 30. Round | 19/03/2022 | Kilmarnock FC | - | Queen Of The South | 2:1 | ||||
| 31. Round | 26/03/2022 | Kilmarnock FC | - | Partick Thistle | 2:1 | ||||
| 32. Round | 01/04/2022 | Greenock Morton FC | - | Kilmarnock FC | 1:1 | |
Scotland