| 1. Round | 03/08/2019 | Ross County FC | - | Hamilton Academical | 3:0 | ||||
| 2. Round | 10/08/2019 | Heart of Midlothian | - | Ross County FC | 0:0 | ||||
| 3. Round | 24/08/2019 | Ross County FC | - | Livingston FC | 1:4 | ||||
| 4. Round | 31/08/2019 | Aberdeen FC | - | Ross County FC | 3:0 | ||||
| 5. Round | 14/09/2019 | Ross County FC | - | St. Mirren FC | 2:1 | ||||
| 6. Round | 21/09/2019 | Motherwell FC | - | Ross County FC | 1:2 | ||||
| 7. Round | 28/09/2019 | Kilmarnock FC | - | Ross County FC | 0:0 | ||||
| 8. Round | 05/10/2019 | Ross County FC | - | St. Johnstone FC | 2:2 | ||||
| 9. Round | 19/10/2019 | Celtic FC | - | Ross County FC | 6:0 | ||||
| 10. Round | 26/10/2019 | Hibernian FC | - | Ross County FC | 2:2 | ||||
| 11. Round | 30/10/2019 | Ross County FC | - | Rangers FC | 0:4 | ||||
| 12. Round | 02/11/2019 | Hamilton Academical | - | Ross County FC | 2:2 | ||||
| 13. Round | 09/11/2019 | Ross County FC | - | Aberdeen FC | 1:3 | ||||
| 27. Round | 15/02/2020 | Ross County FC | - | St. Johnstone FC | 1:1 | ||||
| 28. Round | 22/02/2020 | Aberdeen FC | - | Ross County FC | 1:2 | ||||
| 29. Round | 04/03/2020 | Motherwell FC | - | Ross County FC | 4:1 | ||||
| 30. Round | 08/03/2020 | Ross County FC | - | Rangers FC | 0:1 |
Scotland