| 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 |  |
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| 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 |
Scotland