| 2. Round | 07/08/2021 | Inverness CT | - | Raith Rovers | 1:0 | ||||
| 6. Round | 18/09/2021 | Greenock Morton FC | - | Raith Rovers | 0:1 | ||||
| 8. Round | 02/10/2021 | Kilmarnock FC | - | Raith Rovers | 1:3 | ||||
| 9. Round | 16/10/2021 | Raith Rovers | - | Arbroath FC | 2:1 | ||||
| 10. Round | 23/10/2021 | Raith Rovers | - | Inverness CT | 1:1 | ||||
| 11. Round | 26/10/2021 | Dunfermline Athletic | - | Raith Rovers | 1:1 | ||||
| 12. Round | 30/10/2021 | Raith Rovers | - | Ayr United | 2:1 | ||||
| 13. Round | 06/11/2021 | Queen Of The South | - | Raith Rovers | 1:1 |  |
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| 14. Round | 13/11/2021 | Hamilton Academical | - | Raith Rovers | 0:3 | ||||
| 15. Round | 20/11/2021 | Raith Rovers | - | Greenock Morton FC | 2:1 | ||||
| 16. Round | 04/12/2021 | Arbroath FC | - | Raith Rovers | 0:0 | |
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| 17. Round | 11/12/2021 | Raith Rovers | - | Kilmarnock FC | 1:0 | ||||
| 19. Round | 26/12/2021 | Ayr United | - | Raith Rovers | 2:0 | |
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| 21. Round | 02/01/2022 | Raith Rovers | - | Dunfermline Athletic | 0:0 | ||||
| 24. Round | 28/01/2022 | Greenock Morton FC | - | Raith Rovers | 2:2 | ||||
| 25. Round | 05/02/2022 | Raith Rovers | - | Hamilton Academical | 0:0 |
England