1. Round | 05/08/2023 | Queen Of The South | - | Alloa Athletic | 3:4 | ||||
6. Round | 16/09/2023 | Hamilton Academical | - | Alloa Athletic | 2:1 | ||||
7. Round | 23/09/2023 | Annan Athletic | - | Alloa Athletic | 1:1 | ||||
8. Round | 30/09/2023 | Alloa Athletic | - | Edinburgh City | 1:1 | ||||
9. Round | 07/10/2023 | Montrose FC | - | Alloa Athletic | 2:1 | ||||
10. Round | 21/10/2023 | Alloa Athletic | - | Kelty Hearts | 3:1 | ||||
11. Round | 28/10/2023 | Falkirk FC | - | Alloa Athletic | 3:0 | ||||
28. Round | 09/03/2024 | Alloa Athletic | - | Kelty Hearts | 3:0 | ||||
36. Round | 04/05/2024 | Falkirk FC | - | Alloa Athletic | 2:2 |