| 1. Round | 05/08/2023 | Falkirk FC | - | Annan Athletic | 3:0 | ||||
| 2. Round | 12/08/2023 | Annan Athletic | - | Montrose FC | 1:3 | ||||
| 6. Round | 16/09/2023 | Annan Athletic | - | Stirling Albion FC | 3:0 | ||||
| 7. Round | 23/09/2023 | Annan Athletic | - | Alloa Athletic | 1:1 |  |
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| 8. Round | 29/09/2023 | Hamilton Academical | - | Annan Athletic | 5:0 | ||||
| 9. Round | 07/10/2023 | Cove Rangers | - | Annan Athletic | 3:2 |  |
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| 10. Round | 21/10/2023 | Annan Athletic | - | Queen Of The South | 0:1 | ||||
| 11. Round | 28/10/2023 | Edinburgh City | - | Annan Athletic | 3:2 | ||||
| 12. Round | 04/11/2023 | Annan Athletic | - | Kelty Hearts | 2:2 | |
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| 13. Round | 11/11/2023 | Montrose FC | - | Annan Athletic | 1:1 | ||||
| 14. Round | 28/11/2023 | Annan Athletic | - | Hamilton Academical | 1:2 | |
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| 16. Round | 09/12/2023 | Annan Athletic | - | Cove Rangers | 1:3 | |
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| 17. Round | 16/12/2023 | Stirling Albion FC | - | Annan Athletic | 1:1 | ||||
| 19. Round | 30/12/2023 | Queen Of The South | - | Annan Athletic | 2:1 |
Scotland