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 | ||||
25. Round | 17/02/2024 | Annan Athletic | - | Stirling Albion FC | 2:1 | ||||
26. Round | 24/02/2024 | Cove Rangers | - | Annan Athletic | 2:1 | ||||
27. Round | 02/03/2024 | Falkirk FC | - | Annan Athletic | 1:1 |