| 3. Jornada | 13.08.2022 | Dumbarton FC | - | Annan Athletic | 4:0 | ||||
| 4. Jornada | 20.08.2022 | Annan Athletic | - | Stirling Albion FC | 1:2 | ||||
| 9. Jornada | 01.10.2022 | Elgin City | - | Annan Athletic | 5:1 | ||||
| 10. Jornada | 08.10.2022 | Stenhousemuir FC | - | Annan Athletic | 2:2 | ||||
| 7. Jornada | 11.10.2022 | Bonnyrigg Rose Athletic | - | Annan Athletic | 2:0 | ||||
| 11. Jornada | 15.10.2022 | Annan Athletic | - | Stranraer FC | 1:1 | ||||
| 12. Jornada | 29.10.2022 | Annan Athletic | - | Dumbarton FC | 0:1 | ||||
| 14. Jornada | 12.11.2022 | Stirling Albion FC | - | Annan Athletic | 0:2 | ||||
| 18. Jornada | 23.12.2022 | Annan Athletic | - | Albion Rovers | 5:1 | ||||
| 17. Jornada | 21.01.2023 | Annan Athletic | - | Bonnyrigg Rose Athletic | 4:0 | ||||
| 26. Jornada | 25.02.2023 | Albion Rovers | - | Annan Athletic | 0:2 |
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