| 11. Round | 28/10/2023 | Edinburgh City | - | Annan Athletic | 3:2 | ||||
| 16. Round | 09/12/2023 | Edinburgh City | - | Stirling Albion FC | 1:3 | ||||
| 17. Round | 16/12/2023 | Queen Of The South | - | Edinburgh City | 3:1 |  |
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| 18. Round | 23/12/2023 | Cove Rangers | - | Edinburgh City | 7:2 | ||||
| 19. Round | 30/12/2023 | Edinburgh City | - | Hamilton Academical | 2:5 |
Scotland