| 5. Jornada | 02.09.2023 | Kelty Hearts | - | Annan Athletic | 1:1 | ||||
| 6. Jornada | 16.09.2023 | Annan Athletic | - | Stirling Albion FC | 3:0 | ||||
| 7. Jornada | 23.09.2023 | Annan Athletic | - | Alloa Athletic | 1:1 | ||||
| 8. Jornada | 29.09.2023 | Hamilton Academical | - | Annan Athletic | 5:0 | ||||
| 9. Jornada | 07.10.2023 | Cove Rangers | - | Annan Athletic | 3:2 | ||||
| 11. Jornada | 28.10.2023 | Edinburgh City | - | Annan Athletic | 3:2 | ||||
| 12. Jornada | 04.11.2023 | Annan Athletic | - | Kelty Hearts | 2:2 | ||||
| 13. Jornada | 11.11.2023 | Montrose FC | - | Annan Athletic | 1:1 | ||||
| 14. Jornada | 28.11.2023 | Annan Athletic | - | Hamilton Academical | 1:2 | ||||
| 17. Jornada | 16.12.2023 | Stirling Albion FC | - | Annan Athletic | 1:1 | ||||
| 18. Jornada | 23.12.2023 | Annan Athletic | - | Falkirk FC | 0:3 | ||||
| 20. Jornada | 06.01.2024 | Annan Athletic | - | Montrose FC | 2:2 |
Escocia