1. Round | 05/08/2023 | Falkirk FC | - | Annan Athletic | 3:0 | ||||
3. Round | 19/08/2023 | Queen Of The South | - | Annan Athletic | 3:1 | ||||
4. Round | 26/08/2023 | Annan Athletic | - | Edinburgh City | 3:2 | ||||
9. Round | 07/10/2023 | Cove Rangers | - | Annan Athletic | 3:2 | ||||
11. Round | 28/10/2023 | Edinburgh City | - | Annan Athletic | 3:2 |