1. Round | 05/08/2023 | East Fife FC | - | Peterhead FC | 0:3 | ||||
3. Round | 19/08/2023 | East Fife FC | - | Stenhousemuir FC | 0:2 | ||||
8. Round | 30/09/2023 | East Fife FC | - | Forfar Athletic | 1:1 | ||||
10. Round | 21/10/2023 | East Fife FC | - | Stranraer FC | 4:0 | ||||
11. Round | 04/11/2023 | Peterhead FC | - | East Fife FC | 2:0 | ||||
12. Round | 11/11/2023 | East Fife FC | - | Dumbarton FC | 0:1 | ||||
16. Round | 16/12/2023 | Stenhousemuir FC | - | East Fife FC | 2:1 |