| 20. Round | 07/01/2023 | Elgin City | - | East Fife FC | 1:2 |  |
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| 21. Round | 14/01/2023 | East Fife FC | - | Stenhousemuir FC | 1:1 | ||||
| 17. Round | 21/01/2023 | East Fife FC | - | Stranraer FC | 1:3 | ||||
| 22. Round | 28/01/2023 | Annan Athletic | - | East Fife FC | 3:0 | ||||
| 23. Round | 04/02/2023 | East Fife FC | - | Stirling Albion FC | 1:1 | ||||
| 24. Round | 11/02/2023 | Albion Rovers | - | East Fife FC | 0:1 | ||||
| 25. Round | 18/02/2023 | East Fife FC | - | Dumbarton FC | 2:0 | ||||
| 36. Round | 06/05/2023 | Forfar Athletic | - | East Fife FC | 1:0 |
Scotland