1. Round | 05/08/2023 | Stirling Albion FC | - | Edinburgh City | 1:0 | ||||
4. Round | 26/08/2023 | Annan Athletic | - | Edinburgh City | 3:2 | ||||
5. Round | 02/09/2023 | Edinburgh City | - | Falkirk FC | 0:2 | ||||
6. Round | 16/09/2023 | Montrose FC | - | Edinburgh City | 5:2 | ||||
7. Round | 23/09/2023 | Edinburgh City | - | Cove Rangers | 2:2 | ||||
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 | ||||
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 | ||||
17. Round | 16/12/2023 | Queen Of The South | - | Edinburgh City | 3:1 | ||||
18. Round | 23/12/2023 | Cove Rangers | - | Edinburgh City | 7:2 |