| 1. Round | 05/08/2023 | Dunfermline Athletic | - | Airdrieonians FC | 2:1 | ||||
| 2. Round | 12/08/2023 | Dundee United | - | Dunfermline Athletic | 1:1 | ||||
| 3. Round | 26/08/2023 | Dunfermline Athletic | - | Raith Rovers | 0:1 | ||||
| 4. Round | 02/09/2023 | Inverness CT | - | Dunfermline Athletic | 1:1 | ||||
| 10. Round | 28/10/2023 | Raith Rovers | - | Dunfermline Athletic | 1:0 | ||||
| 18. Round | 30/12/2023 | Ayr United | - | Dunfermline Athletic | 2:2 | ||||
| 28. Round | 09/03/2024 | Raith Rovers | - | Dunfermline Athletic | 2:0 |  |
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| 29. Round | 15/03/2024 | Dunfermline Athletic | - | Dundee United | 3:1 | ||||
| 30. Round | 23/03/2024 | Greenock Morton FC | - | Dunfermline Athletic | 0:1 | ||||
| 31. Round | 30/03/2024 | Arbroath FC | - | Dunfermline Athletic | 2:3 | ||||
| 32. Round | 06/04/2024 | Dunfermline Athletic | - | Partick Thistle | 1:1 | |
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| 33. Round | 13/04/2024 | Airdrieonians FC | - | Dunfermline Athletic | 2:1 | ||||
| 34. Round | 20/04/2024 | Dunfermline Athletic | - | Queen's Park FC | 0:0 | ||||
| 35. Round | 27/04/2024 | Dunfermline Athletic | - | Inverness CT | 1:1 |  |
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Scotland