| League Cup | 21/07/18 | Raith Rovers | - | Heart of Midlothian | 2:4 pso | ||||
| ScPS | 22/09/18 | Heart of Midlothian | - | Livingston FC | 0:0 | ||||
| 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 | ||||
| ScPS | 04/08/19 | Aberdeen FC | - | Heart of Midlothian | 3:2 | ||||
| ScPS | 13/12/20 | Celtic FC | - | Kilmarnock FC | 2:0 | ||||
| ScPS | 13/02/21 | Rangers FC | - | Kilmarnock FC | 1:0 | ||||
| ScPS | 20/02/21 | Aberdeen FC | - | Kilmarnock FC | 1:0 | ||||
| FA Cup | 26/04/21 | Kilmarnock FC | - | St. Mirren FC | 4:5 pso |
Ireland