Groep A | 13.07.2019 | Cowdenbeath FC | - | East Fife FC | 2:0 | ||||
Groep A | 20.07.2019 | East Fife FC | - | Stenhousemuir FC | 2:0 | ||||
Groep A | 23.07.2019 | Dundee United | - | East Fife FC | 0:2 | ||||
Groep A | 27.07.2019 | East Fife FC | - | Heart of Midlothian | 7:6 d.p. | ||||
Achtste finale | 18.08.2019 | East Fife FC | - | Rangers FC | 0:3 |