| Grupo C | 21.07.2018 | Raith Rovers | - | Heart of Midlothian | 2:4 pn. | ||||
| Grupo C | 24.07.2018 | Heart of Midlothian | - | Cowdenbeath FC | 5:0 |  |
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| Grupo C | 29.07.2018 | Heart of Midlothian | - | Inverness CT | 5:0 | |
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| Octavos de final | 18.08.2018 | Dunfermline Athletic | - | Heart of Midlothian | 0:1 | ||||
| Cuartos de final | 26.09.2018 | Heart of Midlothian | - | Motherwell FC | 4:2 | |
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| Semifinales | 28.10.2018 | Heart of Midlothian | - | Celtic FC | 0:3 |
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