1. Round | 05/08/2023 | Falkirk FC | - | Annan Athletic | 3:0 | ||||
20. Round | 06/01/2024 | Annan Athletic | - | Montrose FC | 2:2 | ||||
21. Round | 13/01/2024 | Kelty Hearts | - | Annan Athletic | 1:1 | ||||
15. Round | 13/02/2024 | Alloa Athletic | - | Annan Athletic | 2:1 | ||||
25. Round | 17/02/2024 | Annan Athletic | - | Stirling Albion FC | 2:1 | ||||
29. Round | 16/03/2024 | Montrose FC | - | Annan Athletic | 1:1 | ||||
33. Round | 13/04/2024 | Annan Athletic | - | Cove Rangers | 4:2 | ||||
35. Round | 27/04/2024 | Annan Athletic | - | Falkirk FC | 3:3 |