| Group A | 12/07/2019 | Heart of Midlothian | - | Dundee United | 5:3 pso | ||||
| Group A | 16/07/2019 | Cowdenbeath FC | - | Heart of Midlothian | 0:2 | ||||
| Group A | 24/07/2019 | Heart of Midlothian | - | Stenhousemuir FC | 2:1 | ||||
| Group A | 27/07/2019 | East Fife FC | - | Heart of Midlothian | 7:6 pso | ||||
| Round of 16 | 16/08/2019 | Motherwell FC | - | Heart of Midlothian | 1:2 | ||||
| Quarter-finals | 25/09/2019 | Heart of Midlothian | - | Aberdeen FC | 3:0 pso | ||||
| Semi-finals | 03/11/2019 | Rangers FC | - | Heart of Midlothian | 3:0 |  |
England