| 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 | ||||
| 5. Round | 16/09/2023 | Queen's Park FC | - | Dunfermline Athletic | 0:2 |  |
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| 6. Round | 23/09/2023 | Dunfermline Athletic | - | Greenock Morton FC | 3:1 | ||||
| 7. Round | 30/09/2023 | Partick Thistle | - | Dunfermline Athletic | 3:0 | ||||
| 13. Round | 10/11/2023 | Dunfermline Athletic | - | Dundee United | 1:2 | |
Scotland