| 1. Round | 03/08/2024 | Cove Rangers | - | Annan Athletic | 1:3 | ||||
| 2. Round | 10/08/2024 | Annan Athletic | - | Inverness CT | 1:0 |  |
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| 3. Round | 17/08/2024 | Queen Of The South | - | Annan Athletic | 2:0 |  |
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| 4. Round | 24/08/2024 | Annan Athletic | - | Alloa Athletic | 0:1 | ||||
| 7. Round | 21/09/2024 | Arbroath FC | - | Annan Athletic | 2:0 | ||||
| 8. Round | 28/09/2024 | Kelty Hearts | - | Annan Athletic | 3:0 | ||||
| 9. Round | 05/10/2024 | Annan Athletic | - | Montrose FC | 1:0 | ||||
| 35. Round | 26/04/2025 | Dumbarton FC | - | Annan Athletic | 3:1 | |
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| 36. Round | 03/05/2025 | Annan Athletic | - | Cove Rangers | 2:4 |
England