| 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 | ||||
| 13. Round | 29/10/2022 | Raith Rovers | - | Partick Thistle | 3:0 | ||||
| 14. Round | 05/11/2022 | Raith Rovers | - | Hamilton Academical | 3:1 | ||||
| 15. Round | 12/11/2022 | Dundee FC | - | Raith Rovers | 2:0 | ||||
| 17. Round | 03/12/2022 | Ayr United | - | Raith Rovers | 2:0 | ||||
| 21. Round | 06/01/2023 | Raith Rovers | - | Dundee FC | 1:1 | ||||
| 22. Round | 14/01/2023 | Cove Rangers | - | Raith Rovers | 2:2 |
Denmark