4. Round | 26/08/2023 | Stenhousemuir FC | - | Dumbarton FC | 2:4 | ||||
6. Round | 16/09/2023 | Elgin City | - | Dumbarton FC | 2:0 | ||||
7. Round | 23/09/2023 | Dumbarton FC | - | Peterhead FC | 0:1 | ||||
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 | ||||
15. Round | 09/12/2023 | Dumbarton FC | - | Stenhousemuir FC | 0:1 | ||||
16. Round | 16/12/2023 | Forfar Athletic | - | Dumbarton FC | 2:4 | ||||
17. Round | 23/12/2023 | Dumbarton FC | - | Clyde FC | 4:4 | ||||
19. Round | 06/01/2024 | Dumbarton FC | - | East Fife FC | 1:2 | ||||
20. Round | 13/01/2024 | Bonnyrigg Rose Athletic | - | Dumbarton FC | 1:1 |