| 23. Jornada | 04.02.2023 | Bonnyrigg Rose Athletic | - | Annan Athletic | 1:2 | ||||
| 24. Jornada | 11.02.2023 | Dumbarton FC | - | Annan Athletic | 2:1 | ||||
| 25. Jornada | 18.02.2023 | Annan Athletic | - | Stirling Albion FC | 2:2 |  |
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| 26. Jornada | 25.02.2023 | Albion Rovers | - | Annan Athletic | 0:2 | ||||
| 27. Jornada | 04.03.2023 | Annan Athletic | - | Stenhousemuir FC | 2:3 | ||||
| 28. Jornada | 11.03.2023 | Annan Athletic | - | Elgin City | 4:1 |  |
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| 29. Jornada | 18.03.2023 | Forfar Athletic | - | Annan Athletic | 2:1 | |
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| 30. Jornada | 25.03.2023 | Annan Athletic | - | Stranraer FC | 0:0 | ||||
| 31. Jornada | 01.04.2023 | East Fife FC | - | Annan Athletic | 0:1 | |
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| 32. Jornada | 08.04.2023 | Annan Athletic | - | Dumbarton FC | 3:1 | |
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| 33. Jornada | 15.04.2023 | Annan Athletic | - | Albion Rovers | 4:0 | ||||
| 36. Jornada | 06.05.2023 | Stenhousemuir FC | - | Annan Athletic | 2:1 |
Escocia