| 19. Round | 30/12/2023 | Queen Of The South | - | Annan Athletic | 2:1 | ||||
| 20. Round | 06/01/2024 | Annan Athletic | - | Montrose FC | 2:2 | ||||
| 21. Round | 13/01/2024 | Kelty Hearts | - | Annan Athletic | 1:1 |  |
|||
| 22. Round | 27/01/2024 | Annan Athletic | - | Edinburgh City | 3:0 | ||||
| 23. Round | 03/02/2024 | Annan Athletic | - | Alloa Athletic | 2:3 | ||||
| 24. Round | 10/02/2024 | Hamilton Academical | - | Annan Athletic | 2:3 | ||||
| 15. Round | 13/02/2024 | Alloa Athletic | - | Annan Athletic | 2:1 | ||||
| 27. Round | 02/03/2024 | Falkirk FC | - | Annan Athletic | 1:1 |
England