| 1. Jornada | 05.08.2023 | Falkirk FC | - | Annan Athletic | 3:0 | ||||
| 2. Jornada | 12.08.2023 | Annan Athletic | - | Montrose FC | 1:3 | ||||
| 3. Jornada | 19.08.2023 | Queen Of The South | - | Annan Athletic | 3:1 | ||||
| 4. Jornada | 26.08.2023 | Annan Athletic | - | Edinburgh City | 3:2 | ||||
| 5. Jornada | 02.09.2023 | Kelty Hearts | - | Annan Athletic | 1:1 | ||||
| 14. Jornada | 28.11.2023 | Annan Athletic | - | Hamilton Academical | 1:2 | ||||
| 16. Jornada | 09.12.2023 | Annan Athletic | - | Cove Rangers | 1:3 | ||||
| 17. Jornada | 16.12.2023 | Stirling Albion FC | - | Annan Athletic | 1:1 | ||||
| 18. Jornada | 23.12.2023 | Annan Athletic | - | Falkirk FC | 0:3 | ||||
| 19. Jornada | 30.12.2023 | Queen Of The South | - | Annan Athletic | 2:1 | ||||
| 28. Jornada | 09.03.2024 | Annan Athletic | - | Queen Of The South | 2:1 |
Inglaterra