Gameplan
| Date | Round | Match | Match | Res. | Attendance | |
|---|---|---|---|---|---|---|
| 30.01.2019 |  | 4. Round | Cowdenbeath FC - Rangers FC | - RAN | 1:3 | 4.116 |
| 13.07.2019 |  | Group A | Cowdenbeath FC - East Fife | - Eas | 2:0 | 469 |
| 16.07.2019 | | Group A | Cowdenbeath FC - Hearts FC | - HEA | 0:2 | 2.311 |
Central Park