| 2. Round | 12/08/2023 | Annan Athletic | - | Montrose FC | 1:3 |  |
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| 3. Round | 19/08/2023 | Queen Of The South | - | Annan Athletic | 3:1 | ||||
| 4. Round | 26/08/2023 | Annan Athletic | - | Edinburgh City | 3:2 | ||||
| 5. Round | 02/09/2023 | Kelty Hearts | - | Annan Athletic | 1:1 | ||||
| 8. Round | 29/09/2023 | Hamilton Academical | - | Annan Athletic | 5:0 |
England