| 3. Round | 13/08/2022 | Dumbarton FC | - | Annan Athletic | 4:0 | ||||
| 4. Round | 20/08/2022 | Annan Athletic | - | Stirling Albion FC | 1:2 | ||||
| 9. Round | 01/10/2022 | Elgin City | - | Annan Athletic | 5:1 | ||||
| 10. Round | 08/10/2022 | Stenhousemuir FC | - | Annan Athletic | 2:2 | ||||
| 7. Round | 11/10/2022 | Bonnyrigg Rose Athletic | - | Annan Athletic | 2:0 | ||||
| 11. Round | 15/10/2022 | Annan Athletic | - | Stranraer FC | 1:1 | ||||
| 12. Round | 29/10/2022 | Annan Athletic | - | Dumbarton FC | 0:1 | ||||
| 14. Round | 12/11/2022 | Stirling Albion FC | - | Annan Athletic | 0:2 | ||||
| 18. Round | 23/12/2022 | Annan Athletic | - | Albion Rovers | 5:1 | ||||
| 17. Round | 21/01/2023 | Annan Athletic | - | Bonnyrigg Rose Athletic | 4:0 | ||||
| 26. Round | 25/02/2023 | Albion Rovers | - | Annan Athletic | 0:2 |
Scotland