13. Round | 11/11/2023 | Montrose FC | - | Annan Athletic | 1:1 | ||||
14. Round | 28/11/2023 | Annan Athletic | - | Hamilton Academical | 1:2 | ||||
16. Round | 09/12/2023 | Annan Athletic | - | Cove Rangers | 1:3 | ||||
17. Round | 16/12/2023 | Stirling Albion FC | - | Annan Athletic | 1:1 | ||||
18. Round | 23/12/2023 | Annan Athletic | - | Falkirk FC | 0:3 | ||||
19. Round | 30/12/2023 | Queen Of The South | - | Annan Athletic | 2:1 | ||||
21. Round | 13/01/2024 | Kelty Hearts | - | Annan Athletic | 1:1 | ||||
22. Round | 27/01/2024 | Annan Athletic | - | Edinburgh City | 3:0 | ||||
29. Round | 16/03/2024 | Montrose FC | - | Annan Athletic | 1:1 | ||||
30. Round | 23/03/2024 | Annan Athletic | - | Kelty Hearts | 3:2 |