| 2. Round | 06/08/2022 | Annan Athletic | - | Stenhousemuir FC | 2:1 |  |
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| 3. Round | 13/08/2022 | Dumbarton FC | - | Annan Athletic | 4:0 |  |
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| 4. Round | 20/08/2022 | Annan Athletic | - | Stirling Albion FC | 1:2 | ||||
| 5. Round | 27/08/2022 | Albion Rovers | - | Annan Athletic | 2:2 | ||||
| 6. Round | 03/09/2022 | Annan Athletic | - | Forfar Athletic | 2:1 | |
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| 10. Round | 08/10/2022 | Stenhousemuir FC | - | Annan Athletic | 2:2 | ||||
| 11. Round | 15/10/2022 | Annan Athletic | - | Stranraer FC | 1:1 | |
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| 14. Round | 12/11/2022 | Stirling Albion FC | - | Annan Athletic | 0:2 | |
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| 15. Round | 19/11/2022 | Annan Athletic | - | Elgin City | 1:3 | ||||
| 19. Round | 26/11/2022 | Stranraer FC | - | Annan Athletic | 1:1 | |
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| 27. Round | 04/03/2023 | Annan Athletic | - | Stenhousemuir FC | 2:3 | ||||
| 30. Round | 25/03/2023 | Annan Athletic | - | Stranraer FC | 0:0 | ||||
| 31. Round | 01/04/2023 | East Fife FC | - | Annan Athletic | 0:1 | |
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| 32. Round | 08/04/2023 | Annan Athletic | - | Dumbarton FC | 3:1 | ||||
| 33. Round | 15/04/2023 | Annan Athletic | - | Albion Rovers | 4:0 | ||||
| 34. Round | 22/04/2023 | Stirling Albion FC | - | Annan Athletic | 3:1 | ||||
| 35. Round | 29/04/2023 | Annan Athletic | - | Bonnyrigg Rose Athletic | 0:0 |
England