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