| ScPS | 20/10/18 | Heart of Midlothian | - | Aberdeen FC | 2:1 |  |
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| ScPS | 29/12/18 | Hibernian FC | - | Heart of Midlothian | 0:1 | |
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| FA Cup | 10/02/19 | Heart of Midlothian | - | Auchinleck Talbot | 4:0 | ||||
| ScPS | 03/04/19 | Rangers FC | - | Heart of Midlothian | 3:0 | ||||
| ScPS | 04/05/19 | Heart of Midlothian | - | Kilmarnock FC | 0:1 | ||||
| League Cup | 12/07/19 | Heart of Midlothian | - | Dundee United | 5:3 pso | ||||
| League Cup | 25/09/19 | Heart of Midlothian | - | Aberdeen FC | 3:0 pso | ||||
| ScPS | 20/10/19 | Heart of Midlothian | - | Rangers FC | 1:1 | |
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| ScPS | 15/02/20 | Heart of Midlothian | - | Hamilton Academical | 2:2 | ||||
| ScPS | 03/03/20 | Hibernian FC | - | Heart of Midlothian | 1:3 |  |
England