| 1. Ronde | 05.08.2023 | Bonnyrigg Rose Athletic | - | Dumbarton FC | 1:1 | ||||
| 2. Ronde | 12.08.2023 | Dumbarton FC | - | The Spartans FC | 1:1 | ||||
| 3. Ronde | 19.08.2023 | Dumbarton FC | - | Forfar Athletic | 3:1 | ||||
| 5. Ronde | 02.09.2023 | Dumbarton FC | - | East Fife FC | 1:0 | ||||
| 6. Ronde | 16.09.2023 | Elgin City | - | Dumbarton FC | 2:0 | ||||
| 7. Ronde | 23.09.2023 | Dumbarton FC | - | Peterhead FC | 0:1 |  |
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| 8. Ronde | 30.09.2023 | Dumbarton FC | - | Stranraer FC | 3:1 | |
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| 9. Ronde | 07.10.2023 | Clyde FC | - | Dumbarton FC | 0:4 | ||||
| 10. Ronde | 21.10.2023 | The Spartans FC | - | Dumbarton FC | 2:0 | ||||
| 11. Ronde | 04.11.2023 | Dumbarton FC | - | Bonnyrigg Rose Athletic | 4:0 |  |
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| 12. Ronde | 11.11.2023 | East Fife FC | - | Dumbarton FC | 0:1 | |
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| 15. Ronde | 09.12.2023 | Dumbarton FC | - | Stenhousemuir FC | 0:1 | ||||
| 16. Ronde | 16.12.2023 | Forfar Athletic | - | Dumbarton FC | 2:4 | |
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| 17. Ronde | 23.12.2023 | Dumbarton FC | - | Clyde FC | 4:4 | ||||
| 19. Ronde | 06.01.2024 | Dumbarton FC | - | East Fife FC | 1:2 | |
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| 14. Ronde | 09.01.2024 | Peterhead FC | - | Dumbarton FC | 3:1 | ||||
| 20. Ronde | 13.01.2024 | Bonnyrigg Rose Athletic | - | Dumbarton FC | 1:1 | |
Ierland