4. Ronde | 26.08.2023 | Annan Athletic | - | Edinburgh City | 3:2 | ||||
5. Ronde | 02.09.2023 | Kelty Hearts | - | Annan Athletic | 1:1 | ||||
6. Ronde | 16.09.2023 | Annan Athletic | - | Stirling Albion FC | 3:0 | ||||
7. Ronde | 23.09.2023 | Annan Athletic | - | Alloa Athletic | 1:1 | ||||
8. Ronde | 29.09.2023 | Hamilton Academical | - | Annan Athletic | 5:0 | ||||
10. Ronde | 21.10.2023 | Annan Athletic | - | Queen Of The South | 0:1 | ||||
11. Ronde | 28.10.2023 | Edinburgh City | - | Annan Athletic | 3:2 | ||||
13. Ronde | 11.11.2023 | Montrose FC | - | Annan Athletic | 1:1 |