| Group A | 06/10/2020 | Heart of Midlothian | - | Inverness CT | 1:0 | ||||
| Group A | 10/10/2020 | Cowdenbeath FC | - | Heart of Midlothian | 0:1 | ||||
| Group A | 13/10/2020 | Heart of Midlothian | - | Raith Rovers | 3:1 | ||||
| Group A | 10/11/2020 | East Fife FC | - | Heart of Midlothian | 2:3 | ||||
| Round of 16 | 28/11/2020 | Alloa Athletic | - | Heart of Midlothian | 1:0 aet |
Romania