4. Round | 26/08/2023 | Annan Athletic | - | Edinburgh City | 3:2 | ||||
5. Round | 02/09/2023 | Kelty Hearts | - | Annan Athletic | 1:1 | ||||
6. Round | 16/09/2023 | Annan Athletic | - | Stirling Albion FC | 3:0 | ||||
7. Round | 23/09/2023 | Annan Athletic | - | Alloa Athletic | 1:1 | ||||
8. Round | 29/09/2023 | Hamilton Academical | - | Annan Athletic | 5:0 | ||||
10. Round | 21/10/2023 | Annan Athletic | - | Queen Of The South | 0:1 | ||||
11. Round | 28/10/2023 | Edinburgh City | - | Annan Athletic | 3:2 | ||||
13. Round | 11/11/2023 | Montrose FC | - | Annan Athletic | 1:1 |