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 | ||||
13. Round | 09/11/2019 | Ross County FC | - | Aberdeen FC | 1:3 | ||||
14. Round | 23/11/2019 | St. Mirren FC | - | Ross County FC | 2:1 | ||||
15. Round | 01/12/2019 | Ross County FC | - | Celtic FC | 1:4 | ||||
16. Round | 04/12/2019 | Ross County FC | - | Hibernian FC | 2:1 | ||||
18. Round | 14/12/2019 | Ross County FC | - | Kilmarnock FC | 1:0 | ||||
19. Round | 21/12/2019 | Livingston FC | - | Ross County FC | 4:0 | ||||
20. Round | 26/12/2019 | Ross County FC | - | Motherwell FC | 1:2 | ||||
21. Round | 29/12/2019 | St. Johnstone FC | - | Ross County FC | 1:1 | ||||
25. Round | 05/02/2020 | Ross County FC | - | Livingston FC | 2:0 | ||||
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 |