| 1. Round | 02/08/2021 | Kilmarnock FC | - | Ayr United | 2:0 | ||||
| 2. Round | 07/08/2021 | Queen Of The South | - | Kilmarnock FC | 0:1 |  |
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| 3. Round | 21/08/2021 | Hamilton Academical | - | Kilmarnock FC | 0:2 | ||||
| 4. Round | 28/08/2021 | Kilmarnock FC | - | Inverness CT | 0:1 | ||||
| 5. Round | 11/09/2021 | Kilmarnock FC | - | Greenock Morton FC | 1:0 | ||||
| 6. Round | 18/09/2021 | Partick Thistle | - | Kilmarnock FC | 0:2 | ||||
| 7. Round | 24/09/2021 | Arbroath FC | - | Kilmarnock FC | 0:0 | ||||
| 8. Round | 02/10/2021 | Kilmarnock FC | - | Raith Rovers | 1:3 | ||||
| 9. Round | 16/10/2021 | Dunfermline Athletic | - | Kilmarnock FC | 2:2 | ||||
| 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 | ||||
| 25. Round | 04/02/2022 | Arbroath FC | - | Kilmarnock FC | 1:0 | ||||
| 21. Round | 09/02/2022 | Kilmarnock FC | - | Ayr United | 1:2 | ||||
| 27. Round | 26/02/2022 | Dunfermline Athletic | - | Kilmarnock FC | 0:0 |
Scotland