| 25. Ronde | 17.02.2024 | Annan Athletic | - | Stirling Albion FC | 2:1 | ||||
| 26. Ronde | 24.02.2024 | Cove Rangers | - | Annan Athletic | 2:1 | ||||
| 27. Ronde | 02.03.2024 | Falkirk FC | - | Annan Athletic | 1:1 |  |
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| 28. Ronde | 09.03.2024 | Annan Athletic | - | Queen Of The South | 2:1 | ||||
| 30. Ronde | 23.03.2024 | Annan Athletic | - | Kelty Hearts | 3:2 | ||||
| 31. Ronde | 30.03.2024 | Alloa Athletic | - | Annan Athletic | 1:1 | ||||
| 32. Ronde | 06.04.2024 | Annan Athletic | - | Hamilton Academical | 1:3 | ||||
| 33. Ronde | 13.04.2024 | Annan Athletic | - | Cove Rangers | 4:2 | ||||
| 34. Ronde | 20.04.2024 | Edinburgh City | - | Annan Athletic | 1:2 | ||||
| 35. Ronde | 27.04.2024 | Annan Athletic | - | Falkirk FC | 3:3 | ||||
| 36. Ronde | 04.05.2024 | Stirling Albion FC | - | Annan Athletic | 1:1 |
Schotland