| 27. Round | 02/03/2024 | Dumbarton FC | - | Peterhead FC | 1:0 | ||||
| 18. Round | 05/03/2024 | Stranraer FC | - | Dumbarton FC | 5:0 | ||||
| 28. Round | 09/03/2024 | East Fife FC | - | Dumbarton FC | 3:2 | ||||
| 29. Round | 16/03/2024 | The Spartans FC | - | Dumbarton FC | 2:6 |  |
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| 30. Round | 23/03/2024 | Dumbarton FC | - | Bonnyrigg Rose Athletic | 2:0 | ||||
| 32. Round | 06/04/2024 | Forfar Athletic | - | Dumbarton FC | 0:2 | ||||
| 34. Round | 20/04/2024 | Stranraer FC | - | Dumbarton FC | 0:0 | ||||
| 35. Round | 27/04/2024 | Dumbarton FC | - | Elgin City | 2:2 | |
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| 36. Round | 04/05/2024 | Peterhead FC | - | Dumbarton FC | 2:1 |
Scotland