| 1. Round | 05/08/2023 | Bonnyrigg Rose Athletic | - | Dumbarton FC | 1:1 | ||||
| 2. Round | 12/08/2023 | Clyde FC | - | Bonnyrigg Rose Athletic | 0:2 | ||||
| 3. Round | 19/08/2023 | Bonnyrigg Rose Athletic | - | Stranraer FC | 1:1 |  |
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| 4. Round | 26/08/2023 | Forfar Athletic | - | Bonnyrigg Rose Athletic | 1:2 | |
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| 5. Round | 02/09/2023 | Bonnyrigg Rose Athletic | - | Elgin City | 5:1 |  |
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| 6. Round | 16/09/2023 | Peterhead FC | - | Bonnyrigg Rose Athletic | 2:1 | ||||
| 7. Round | 23/09/2023 | Bonnyrigg Rose Athletic | - | Stenhousemuir FC | 0:1 | ||||
| 8. Round | 30/09/2023 | The Spartans FC | - | Bonnyrigg Rose Athletic | 2:2 | ||||
| 10. Round | 21/10/2023 | Bonnyrigg Rose Athletic | - | Clyde FC | 3:2 | |
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| 11. Round | 04/11/2023 | Dumbarton FC | - | Bonnyrigg Rose Athletic | 4:0 | ||||
| 12. Round | 11/11/2023 | Elgin City | - | Bonnyrigg Rose Athletic | 2:0 | ||||
| 13. Round | 18/11/2023 | Bonnyrigg Rose Athletic | - | Forfar Athletic | 0:2 | ||||
| 16. Round | 16/12/2023 | Stranraer FC | - | Bonnyrigg Rose Athletic | 3:1 | |
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| 30. Round | 23/03/2024 | Dumbarton FC | - | Bonnyrigg Rose Athletic | 2:0 | ||||
| 32. Round | 06/04/2024 | Bonnyrigg Rose Athletic | - | Peterhead FC | 2:2 |
Scotland