Gameplan
| Date | Round | Match | Match | Res. | Attendance | |
|---|---|---|---|---|---|---|
| 19.01.2019 |  | 4. Round | East Fife - Morton | Eas - Mor | 2:1 | 903 |
| 09.02.2019 | | Round of 16 | East Fife - Partick Thistle | Eas - PT | 0:1 | 1.724 |
| 20.07.2019 |  | Group A | East Fife - Stenhousemuir | Eas - Ste | 2:0 | 308 |
| 27.07.2019 | | Group A | East Fife - Hearts FC | Eas - HEA | 7:6 | 1.998 |
| 18.08.2019 | | Round of 16 | East Fife - Rangers FC | Eas - RAN | 0:3 | 1.991 |