| 21. Round | 13/01/2024 | Raith Rovers | - | Queen's Park FC | 1:2 | ||||
| 22. Round | 27/01/2024 | Raith Rovers | - | Inverness CT | 2:3 | ||||
| 25. Round | 24/02/2024 | Ayr United | - | Raith Rovers | 1:2 | ||||
| 26. Round | 27/02/2024 | Raith Rovers | - | Greenock Morton FC | 0:0 |  |
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| 27. Round | 01/03/2024 | Arbroath FC | - | Raith Rovers | 3:2 | ||||
| 23. Round | 12/03/2024 | Partick Thistle | - | Raith Rovers | 0:1 | ||||
| 29. Round | 16/03/2024 | Queen's Park FC | - | Raith Rovers | 0:0 | |
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| 31. Round | 30/03/2024 | Dundee United | - | Raith Rovers | 2:0 | |
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| 32. Round | 06/04/2024 | Raith Rovers | - | Ayr United | 2:1 | ||||
| 30. Round | 09/04/2024 | Raith Rovers | - | Airdrieonians FC | 1:3 | ||||
| 33. Round | 13/04/2024 | Raith Rovers | - | Partick Thistle | 0:0 | ||||
| 35. Round | 27/04/2024 | Greenock Morton FC | - | Raith Rovers | 0:0 | ||||
| 36. Round | 03/05/2024 | Raith Rovers | - | Arbroath FC | 5:0 |
Scotland