| 3. Ronde | 26.08.2023 | Dunfermline Athletic | - | Raith Rovers | 0:1 | ||||
| 4. Ronde | 02.09.2023 | Raith Rovers | - | Queen's Park FC | 3:2 | ||||
| 5. Ronde | 16.09.2023 | Raith Rovers | - | Inverness CT | 1:0 |  |
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| 6. Ronde | 23.09.2023 | Airdrieonians FC | - | Raith Rovers | 1:0 |  |
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| 7. Ronde | 30.09.2023 | Ayr United | - | Raith Rovers | 1:2 | ||||
| 8. Ronde | 07.10.2023 | Raith Rovers | - | Dundee United | 1:1 | ||||
| 13. Ronde | 11.11.2023 | Queen's Park FC | - | Raith Rovers | 2:3 | ||||
| 14. Ronde | 02.12.2023 | Inverness CT | - | Raith Rovers | 1:2 | |
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| 15. Ronde | 08.12.2023 | Raith Rovers | - | Partick Thistle | 4:3 | ||||
| 9. Ronde | 13.12.2023 | Arbroath FC | - | Raith Rovers | 1:2 | ||||
| 16. Ronde | 16.12.2023 | Dundee United | - | Raith Rovers | 0:1 | ||||
| 17. Ronde | 22.12.2023 | Raith Rovers | - | Ayr United | 4:4 | ||||
| 18. Ronde | 30.12.2023 | Raith Rovers | - | Arbroath FC | 2:2 | ||||
| 19. Ronde | 02.01.2024 | Dunfermline Athletic | - | Raith Rovers | 1:2 | ||||
| 20. Ronde | 06.01.2024 | Airdrieonians FC | - | Raith Rovers | 1:0 | ||||
| 21. Ronde | 13.01.2024 | Raith Rovers | - | Queen's Park FC | 1:2 | |
Schotland