| 17. Round | 21/01/2023 | Annan Athletic | - | Bonnyrigg Rose Athletic | 4:0 | ||||
| 22. Round | 28/01/2023 | Dumbarton FC | - | Bonnyrigg Rose Athletic | 1:0 | ||||
| 25. Round | 28/02/2023 | Bonnyrigg Rose Athletic | - | Forfar Athletic | 1:1 | ||||
| 27. Round | 04/03/2023 | Elgin City | - | Bonnyrigg Rose Athletic | 0:1 | ||||
| 28. Round | 11/03/2023 | Stirling Albion FC | - | Bonnyrigg Rose Athletic | 2:1 | ||||
| 34. Round | 22/04/2023 | Forfar Athletic | - | Bonnyrigg Rose Athletic | 0:1 | ||||
| 35. Round | 29/04/2023 | Annan Athletic | - | Bonnyrigg Rose Athletic | 0:0 |  |
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| 36. Round | 06/05/2023 | Bonnyrigg Rose Athletic | - | Elgin City | 3:0 |
Scotland