13. Ronde | 11.11.2023 | Montrose FC | - | Annan Athletic | 1:1 | ||||
14. Ronde | 28.11.2023 | Annan Athletic | - | Hamilton Academical | 1:2 | ||||
16. Ronde | 09.12.2023 | Annan Athletic | - | Cove Rangers | 1:3 | ||||
17. Ronde | 16.12.2023 | Stirling Albion FC | - | Annan Athletic | 1:1 | ||||
18. Ronde | 23.12.2023 | Annan Athletic | - | Falkirk FC | 0:3 | ||||
19. Ronde | 30.12.2023 | Queen Of The South | - | Annan Athletic | 2:1 | ||||
21. Ronde | 13.01.2024 | Kelty Hearts | - | Annan Athletic | 1:1 | ||||
22. Ronde | 27.01.2024 | Annan Athletic | - | Edinburgh City | 3:0 | ||||
29. Ronde | 16.03.2024 | Montrose FC | - | Annan Athletic | 1:1 | ||||
30. Ronde | 23.03.2024 | Annan Athletic | - | Kelty Hearts | 3:2 |