| 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 | ||||
| 9. Round | 07/10/2023 | Cove Rangers | - | Annan Athletic | 3:2 | ||||
| 11. Round | 28/10/2023 | Edinburgh City | - | Annan Athletic | 3:2 | ||||
| 12. Round | 04/11/2023 | Annan Athletic | - | Kelty Hearts | 2:2 | ||||
| 13. Round | 11/11/2023 | Montrose FC | - | Annan Athletic | 1:1 | ||||
| 14. Round | 28/11/2023 | Annan Athletic | - | Hamilton Academical | 1:2 | ||||
| 17. Round | 16/12/2023 | Stirling Albion FC | - | Annan Athletic | 1:1 | ||||
| 18. Round | 23/12/2023 | Annan Athletic | - | Falkirk FC | 0:3 | ||||
| 20. Round | 06/01/2024 | Annan Athletic | - | Montrose FC | 2:2 |
Scotland