| Grupo A | 16.07.2019 | Cowdenbeath FC | - | Heart of Midlothian | 0:2 | ||||
| Grupo A | 24.07.2019 | Heart of Midlothian | - | Stenhousemuir FC | 2:1 | ||||
| Grupo A | 27.07.2019 | East Fife FC | - | Heart of Midlothian | 7:6 pn. | ||||
| Octavos de final | 16.08.2019 | Motherwell FC | - | Heart of Midlothian | 1:2 | ||||
| Cuartos de final | 25.09.2019 | Heart of Midlothian | - | Aberdeen FC | 3:0 pn. |  |
|||
| Semifinales | 03.11.2019 | Rangers FC | - | Heart of Midlothian | 3:0 |  |
Escocia