| 5. Round | 02/09/2023 | Dumbarton FC | - | East Fife FC | 1:0 | ||||
| 6. Round | 16/09/2023 | East Fife FC | - | Clyde FC | 2:0 | ||||
| 7. Round | 23/09/2023 | The Spartans FC | - | East Fife FC | 2:2 | ||||
| 8. Round | 30/09/2023 | East Fife FC | - | Forfar Athletic | 1:1 | ||||
| 10. Round | 21/10/2023 | East Fife FC | - | Stranraer FC | 4:0 | ||||
| 11. Round | 04/11/2023 | Peterhead FC | - | East Fife FC | 2:0 | ||||
| 12. Round | 11/11/2023 | East Fife FC | - | Dumbarton FC | 0:1 | ||||
| 13. Round | 18/11/2023 | Clyde FC | - | East Fife FC | 0:4 |  |
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| 9. Round | 21/11/2023 | Bonnyrigg Rose Athletic | - | East Fife FC | 4:2 | ||||
| 16. Round | 16/12/2023 | Stenhousemuir FC | - | East Fife FC | 2:1 | ||||
| 18. Round | 30/12/2023 | Forfar Athletic | - | East Fife FC | 0:0 | ||||
| 19. Round | 06/01/2024 | Dumbarton FC | - | East Fife FC | 1:2 |
Scotland