23. Round | 04/02/2023 | Bonnyrigg Rose Athletic | - | Annan Athletic | 1:2 | ||||
24. Round | 11/02/2023 | Dumbarton FC | - | Annan Athletic | 2:1 | ||||
25. Round | 18/02/2023 | Annan Athletic | - | Stirling Albion FC | 2:2 | ||||
26. Round | 25/02/2023 | Albion Rovers | - | Annan Athletic | 0:2 | ||||
27. Round | 04/03/2023 | Annan Athletic | - | Stenhousemuir FC | 2:3 | ||||
28. Round | 11/03/2023 | Annan Athletic | - | Elgin City | 4:1 | ||||
29. Round | 18/03/2023 | Forfar Athletic | - | Annan Athletic | 2:1 | ||||
30. Round | 25/03/2023 | Annan Athletic | - | Stranraer FC | 0:0 | ||||
31. Round | 01/04/2023 | East Fife FC | - | Annan Athletic | 0:1 | ||||
32. Round | 08/04/2023 | Annan Athletic | - | Dumbarton FC | 3:1 | ||||
33. Round | 15/04/2023 | Annan Athletic | - | Albion Rovers | 4:0 | ||||
36. Round | 06/05/2023 | Stenhousemuir FC | - | Annan Athletic | 2:1 |