| 1. Round | 05/08/2023 | Dunfermline Athletic | - | Airdrieonians FC | 2:1 |  |
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| 3. Round | 26/08/2023 | Dunfermline Athletic | - | Raith Rovers | 0:1 | ||||
| 9. Round | 21/10/2023 | Dunfermline Athletic | - | Ayr United | 0:1 | ||||
| 10. Round | 28/10/2023 | Raith Rovers | - | Dunfermline Athletic | 1:0 | ||||
| 17. Round | 23/12/2023 | Arbroath FC | - | Dunfermline Athletic | 1:1 | ||||
| 18. Round | 30/12/2023 | Ayr United | - | Dunfermline Athletic | 2:2 | ||||
| 19. Round | 02/01/2024 | Dunfermline Athletic | - | Raith Rovers | 1:2 |  |
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| 31. Round | 30/03/2024 | Arbroath FC | - | Dunfermline Athletic | 2:3 | ||||
| 34. Round | 20/04/2024 | Dunfermline Athletic | - | Queen's Park FC | 0:0 | ||||
| 36. Round | 03/05/2024 | Ayr United | - | Dunfermline Athletic | 3:3 |
Scotland