| 2. Round | 06/08/2022 | Raith Rovers | - | Dundee FC | 0:1 | ||||
| 3. Round | 13/08/2022 | Raith Rovers | - | Greenock Morton FC | 2:1 |  |
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| 4. Round | 20/08/2022 | Hamilton Academical | - | Raith Rovers | 0:2 | ||||
| 5. Round | 27/08/2022 | Partick Thistle | - | Raith Rovers | 2:1 | ||||
| 6. Round | 03/09/2022 | Raith Rovers | - | Inverness CT | 0:2 | ||||
| 8. Round | 17/09/2022 | Raith Rovers | - | Ayr United | 3:2 | ||||
| 9. Round | 01/10/2022 | Queen's Park FC | - | Raith Rovers | 1:0 | ||||
| 10. Round | 08/10/2022 | Raith Rovers | - | Cove Rangers | 3:0 | ||||
| 11. Round | 15/10/2022 | Greenock Morton FC | - | Raith Rovers | 1:0 | ||||
| 7. Round | 19/10/2022 | Arbroath FC | - | Raith Rovers | 0:1 | ||||
| 12. Round | 22/10/2022 | Inverness CT | - | Raith Rovers | 1:1 | ||||
| 13. Round | 29/10/2022 | Raith Rovers | - | Partick Thistle | 3:0 | |
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| 14. Round | 05/11/2022 | Raith Rovers | - | Hamilton Academical | 3:1 | ||||
| 15. Round | 12/11/2022 | Dundee FC | - | Raith Rovers | 2:0 | ||||
| 16. Round | 19/11/2022 | Raith Rovers | - | Queen's Park FC | 2:5 | |
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| 17. Round | 03/12/2022 | Ayr United | - | Raith Rovers | 2:0 | ||||
| 18. Round | 17/12/2022 | Raith Rovers | - | Arbroath FC | 1:1 | ||||
| 19. Round | 23/12/2022 | Raith Rovers | - | Greenock Morton FC | 2:2 |
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