| 1. Ronde | 05.08.2023 | Falkirk FC | - | Annan Athletic | 3:0 | ||||
| 2. Ronde | 12.08.2023 | Annan Athletic | - | Montrose FC | 1:3 | ||||
| 3. Ronde | 19.08.2023 | Queen Of The South | - | Annan Athletic | 3:1 |  |
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| 5. Ronde | 02.09.2023 | Kelty Hearts | - | Annan Athletic | 1:1 | ||||
| 6. Ronde | 16.09.2023 | Annan Athletic | - | Stirling Albion FC | 3:0 | ||||
| 7. Ronde | 23.09.2023 | Annan Athletic | - | Alloa Athletic | 1:1 | ||||
| 8. Ronde | 29.09.2023 | Hamilton Academical | - | Annan Athletic | 5:0 | |
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| 9. Ronde | 07.10.2023 | Cove Rangers | - | Annan Athletic | 3:2 | ||||
| 10. Ronde | 21.10.2023 | Annan Athletic | - | Queen Of The South | 0:1 |
Schotland