| 1. Jornada | 05.08.2023 | Bonnyrigg Rose Athletic | - | Dumbarton FC | 1:1 | ||||
| 2. Jornada | 12.08.2023 | Dumbarton FC | - | The Spartans FC | 1:1 | ||||
| 3. Jornada | 19.08.2023 | Dumbarton FC | - | Forfar Athletic | 3:1 |  |
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| 4. Jornada | 26.08.2023 | Stenhousemuir FC | - | Dumbarton FC | 2:4 | |
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| 5. Jornada | 02.09.2023 | Dumbarton FC | - | East Fife FC | 1:0 | ||||
| 6. Jornada | 16.09.2023 | Elgin City | - | Dumbarton FC | 2:0 | ||||
| 7. Jornada | 23.09.2023 | Dumbarton FC | - | Peterhead FC | 0:1 | |
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| 9. Jornada | 07.10.2023 | Clyde FC | - | Dumbarton FC | 0:4 | ||||
| 10. Jornada | 21.10.2023 | The Spartans FC | - | Dumbarton FC | 2:0 | ||||
| 11. Jornada | 04.11.2023 | Dumbarton FC | - | Bonnyrigg Rose Athletic | 4:0 | ||||
| 12. Jornada | 11.11.2023 | East Fife FC | - | Dumbarton FC | 0:1 | ||||
| 13. Jornada | 18.11.2023 | Dumbarton FC | - | Elgin City | 1:0 | ||||
| 15. Jornada | 09.12.2023 | Dumbarton FC | - | Stenhousemuir FC | 0:1 | ||||
| 16. Jornada | 16.12.2023 | Forfar Athletic | - | Dumbarton FC | 2:4 | ||||
| 17. Jornada | 23.12.2023 | Dumbarton FC | - | Clyde FC | 4:4 |
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