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 | ||||
4. Round | 26/08/2023 | Stenhousemuir FC | - | Dumbarton FC | 2:4 | ||||
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 |