| Grupo A | 12.07.2019 | Heart of Midlothian | - | Dundee United | 5:3 pn. |  |
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| Grupo A | 27.07.2019 | East Fife FC | - | Heart of Midlothian | 7:6 pn. |  |
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| 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 |
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