| 1. Round | 05/08/2023 | Stirling Albion FC | - | Edinburgh City | 1:0 | ||||
| 2. Round | 12/08/2023 | Edinburgh City | - | Queen Of The South | 1:2 | ||||
| 3. Round | 19/08/2023 | Edinburgh City | - | Hamilton Academical | 0:3 | ||||
| 4. Round | 26/08/2023 | Annan Athletic | - | Edinburgh City | 3:2 | ||||
| 5. Round | 02/09/2023 | Edinburgh City | - | Falkirk FC | 0:2 | ||||
| 8. Round | 30/09/2023 | Alloa Athletic | - | Edinburgh City | 1:1 | ||||
| 9. Round | 07/10/2023 | Edinburgh City | - | Kelty Hearts | 1:4 | ||||
| 10. Round | 21/10/2023 | Hamilton Academical | - | Edinburgh City | 1:1 | ||||
| 11. Round | 28/10/2023 | Edinburgh City | - | Annan Athletic | 3:2 |  |
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| 12. Round | 04/11/2023 | Edinburgh City | - | Montrose FC | 1:5 | ||||
| 13. Round | 11/11/2023 | Falkirk FC | - | Edinburgh City | 2:1 | ||||
| 14. Round | 18/11/2023 | Edinburgh City | - | Alloa Athletic | 3:0 | |
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| 16. Round | 09/12/2023 | Edinburgh City | - | Stirling Albion FC | 1:3 | |
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| 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 | |
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| 19. Round | 30/12/2023 | Edinburgh City | - | Hamilton Academical | 2:5 | |
Ireland