| League Cup | 27.07.19 | East Fife FC | - | Heart of Midlothian | 7:6 pn. |  |
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| ScPS | 30.10.19 | St. Johnstone FC | - | Heart of Midlothian | 1:0 | ||||
| ScPS | 05.02.20 | Heart of Midlothian | - | Kilmarnock FC | 2:3 | |
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| Championship | 16.10.20 | Heart of Midlothian | - | Dundee FC | 6:2 | |
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| Championship | 26.12.20 | Heart of Midlothian | - | Ayr United | 5:3 | ||||
| Championship | 30.04.21 | Raith Rovers | - | Heart of Midlothian | 0:4 |
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