| 1. Round | 05/08/2023 | Bonnyrigg Rose Athletic | - | Dumbarton FC | 1:1 | ||||
| 2. Round | 12/08/2023 | Dumbarton FC | - | The Spartans FC | 1:1 | ||||
| 3. Round | 19/08/2023 | Dumbarton FC | - | Forfar Athletic | 3:1 | ||||
| 5. Round | 02/09/2023 | Dumbarton FC | - | East Fife FC | 1:0 | ||||
| 6. Round | 16/09/2023 | Elgin City | - | Dumbarton FC | 2:0 | ||||
| 7. Round | 23/09/2023 | Dumbarton FC | - | Peterhead FC | 0:1 |  |
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| 8. Round | 30/09/2023 | Dumbarton FC | - | Stranraer FC | 3:1 | |
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| 9. Round | 07/10/2023 | Clyde FC | - | Dumbarton FC | 0:4 | ||||
| 10. Round | 21/10/2023 | The Spartans FC | - | Dumbarton FC | 2:0 | ||||
| 11. Round | 04/11/2023 | Dumbarton FC | - | Bonnyrigg Rose Athletic | 4:0 |  |
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| 12. Round | 11/11/2023 | East Fife FC | - | Dumbarton FC | 0:1 | |
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| 15. Round | 09/12/2023 | Dumbarton FC | - | Stenhousemuir FC | 0:1 | ||||
| 16. Round | 16/12/2023 | Forfar Athletic | - | Dumbarton FC | 2:4 | |
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| 17. Round | 23/12/2023 | Dumbarton FC | - | Clyde FC | 4:4 | ||||
| 19. Round | 06/01/2024 | Dumbarton FC | - | East Fife FC | 1:2 | |
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| 14. Round | 09/01/2024 | Peterhead FC | - | Dumbarton FC | 3:1 | ||||
| 20. Round | 13/01/2024 | Bonnyrigg Rose Athletic | - | Dumbarton FC | 1:1 | |
Ireland