| 19. Round | 02/01/2023 | Forfar Athletic | - | Elgin City | 0:1 |  |
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| 20. Round | 07/01/2023 | Elgin City | - | East Fife FC | 1:2 | ||||
| 21. Round | 14/01/2023 | Elgin City | - | Annan Athletic | 1:1 | ||||
| 22. Round | 28/01/2023 | Stenhousemuir FC | - | Elgin City | 2:0 |  |
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| 23. Round | 04/02/2023 | Elgin City | - | Albion Rovers | 1:1 | ||||
| 25. Round | 18/02/2023 | Elgin City | - | Stranraer FC | 0:1 | |
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| 17. Round | 21/02/2023 | Albion Rovers | - | Elgin City | 3:0 | ||||
| 26. Round | 25/02/2023 | Dumbarton FC | - | Elgin City | 1:2 | ||||
| 27. Round | 04/03/2023 | Elgin City | - | Bonnyrigg Rose Athletic | 0:1 | ||||
| 28. Round | 11/03/2023 | Annan Athletic | - | Elgin City | 4:1 | ||||
| 30. Round | 24/03/2023 | East Fife FC | - | Elgin City | 2:0 | ||||
| 32. Round | 08/04/2023 | Albion Rovers | - | Elgin City | 3:0 | ||||
| 29. Round | 11/04/2023 | Elgin City | - | Stenhousemuir FC | 1:1 | |
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| 33. Round | 15/04/2023 | Elgin City | - | Forfar Athletic | 2:0 | |
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| 34. Round | 22/04/2023 | Stranraer FC | - | Elgin City | 3:1 | |
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| 35. Round | 29/04/2023 | Elgin City | - | Dumbarton FC | 1:0 | ||||
| 36. Round | 06/05/2023 | Bonnyrigg Rose Athletic | - | Elgin City | 3:0 |
Scotland