| ScPS | 10/11/18 | Heart of Midlothian | - | Kilmarnock FC | 0:1 | ||||
| ScPS | 26/12/18 | Heart of Midlothian | - | Hamilton Academical | 2:0 | ||||
| ScPS | 23/02/19 | Heart of Midlothian | - | St. Mirren FC | 1:1 | ||||
| FA Cup | 13/04/19 | Heart of Midlothian | - | Inverness CT | 3:0 |  |
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| ScPS | 04/08/19 | Aberdeen FC | - | Heart of Midlothian | 3:2 |  |
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| ScPS | 01/12/19 | Rangers FC | - | Heart of Midlothian | 5:0 | ||||
| ScPS | 26/12/19 | Heart of Midlothian | - | Hibernian FC | 0:2 | ||||
| FA Cup | 18/01/20 | Heart of Midlothian | - | Airdrieonians FC | 5:0 | |
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| ScPS | 07/03/20 | Heart of Midlothian | - | Motherwell FC | 1:1 |
England