| 1. Ronde | 05.08.2023 | Falkirk FC | - | Annan Athletic | 3:0 | ||||
| 2. Ronde | 12.08.2023 | Annan Athletic | - | Montrose FC | 1:3 | ||||
| 6. Ronde | 16.09.2023 | Annan Athletic | - | Stirling Albion FC | 3:0 | ||||
| 7. Ronde | 23.09.2023 | Annan Athletic | - | Alloa Athletic | 1:1 |  |
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| 8. Ronde | 29.09.2023 | Hamilton Academical | - | Annan Athletic | 5:0 | ||||
| 9. Ronde | 07.10.2023 | Cove Rangers | - | Annan Athletic | 3:2 |  |
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| 10. Ronde | 21.10.2023 | Annan Athletic | - | Queen Of The South | 0:1 | ||||
| 11. Ronde | 28.10.2023 | Edinburgh City | - | Annan Athletic | 3:2 | ||||
| 12. Ronde | 04.11.2023 | Annan Athletic | - | Kelty Hearts | 2:2 | |
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| 13. Ronde | 11.11.2023 | Montrose FC | - | Annan Athletic | 1:1 | ||||
| 14. Ronde | 28.11.2023 | Annan Athletic | - | Hamilton Academical | 1:2 | |
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| 16. Ronde | 09.12.2023 | Annan Athletic | - | Cove Rangers | 1:3 | |
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| 17. Ronde | 16.12.2023 | Stirling Albion FC | - | Annan Athletic | 1:1 | ||||
| 19. Ronde | 30.12.2023 | Queen Of The South | - | Annan Athletic | 2:1 |
Schotland