| Groep A | 16.07.2019 | Cowdenbeath FC | - | Heart of Midlothian | 0:2 |  |
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| Groep A | 24.07.2019 | Heart of Midlothian | - | Stenhousemuir FC | 2:1 | |
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| Groep A | 27.07.2019 | East Fife FC | - | Heart of Midlothian | 7:6 d.p. | ||||
| Achtste finale | 16.08.2019 | Motherwell FC | - | Heart of Midlothian | 1:2 | ||||
| Kwartfinale | 25.09.2019 | Heart of Midlothian | - | Aberdeen FC | 3:0 d.p. | |
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Schotland