| 2. Round | 06/08/2022 | East Fife FC | - | Bonnyrigg Rose Athletic | 0:3 | ||||
| 3. Round | 13/08/2022 | Albion Rovers | - | East Fife FC | 0:1 | ||||
| 4. Round | 20/08/2022 | East Fife FC | - | Forfar Athletic | 1:0 | ||||
| 5. Round | 27/08/2022 | Stranraer FC | - | East Fife FC | 2:2 | ||||
| 6. Round | 03/09/2022 | East Fife FC | - | Dumbarton FC | 0:1 | ||||
| 8. Round | 17/09/2022 | Annan Athletic | - | East Fife FC | 2:2 |  |
|||
| 7. Round | 20/09/2022 | East Fife FC | - | Stenhousemuir FC | 1:2 | ||||
| 9. Round | 01/10/2022 | East Fife FC | - | Stirling Albion FC | 1:2 | |
|||
| 10. Round | 08/10/2022 | Forfar Athletic | - | East Fife FC | 1:3 | ||||
| 11. Round | 15/10/2022 | Bonnyrigg Rose Athletic | - | East Fife FC | 1:4 | |
|||
| 12. Round | 29/10/2022 | East Fife FC | - | Elgin City | 2:1 | ||||
| 13. Round | 05/11/2022 | Stenhousemuir FC | - | East Fife FC | 2:2 | ||||
| 14. Round | 12/11/2022 | East Fife FC | - | Albion Rovers | 2:3 |  |
|||
| 15. Round | 19/11/2022 | Stirling Albion FC | - | East Fife FC | 3:1 | ||||
| 19. Round | 10/12/2022 | East Fife FC | - | Bonnyrigg Rose Athletic | 0:0 |
Portugal