| ScPS | 01/09/18 | Heart of Midlothian | - | St. Mirren FC | 4:1 | ||||
| ScPS | 20/10/18 | Heart of Midlothian | - | Aberdeen FC | 2:1 | ||||
| ScPS | 29/12/18 | Hibernian FC | - | Heart of Midlothian | 0:1 | ||||
| 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 | ||||
| ScPS | 22/08/20 | Rangers FC | - | Kilmarnock FC | 2:0 | ||||
| ScPS | 26/12/20 | Kilmarnock FC | - | Livingston FC | 1:2 | ||||
| ScPS | 02/02/21 | Kilmarnock FC | - | Celtic FC | 0:4 | ||||
| ScPS | 16/05/21 | Hamilton Academical | - | Kilmarnock FC | 0:2 |
Ireland