| League Cup | 27/07/19 | East Fife FC | - | Heart of Midlothian | 7:6 pso |  |
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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 |
Scotland