| 19. Ronde | 30.12.2023 | Queen Of The South | - | Annan Athletic | 2:1 | ||||
| 20. Ronde | 06.01.2024 | Annan Athletic | - | Montrose FC | 2:2 | ||||
| 21. Ronde | 13.01.2024 | Kelty Hearts | - | Annan Athletic | 1:1 |  |
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| 22. Ronde | 27.01.2024 | Annan Athletic | - | Edinburgh City | 3:0 | ||||
| 23. Ronde | 03.02.2024 | Annan Athletic | - | Alloa Athletic | 2:3 | ||||
| 24. Ronde | 10.02.2024 | Hamilton Academical | - | Annan Athletic | 2:3 | ||||
| 15. Ronde | 13.02.2024 | Alloa Athletic | - | Annan Athletic | 2:1 | ||||
| 27. Ronde | 02.03.2024 | Falkirk FC | - | Annan Athletic | 1:1 |
Engeland