| 2. Round | 11/08/2019 | Rangers FC | - | Hibernian FC | 6:1 | ||||
| 5. Round | 14/09/2019 | Rangers FC | - | Livingston FC | 3:1 | ||||
| 11. Round | 30/10/2019 | Ross County FC | - | Rangers FC | 0:4 | ||||
| 26. Round | 12/02/2020 | Kilmarnock FC | - | Rangers FC | 2:1 | ||||
| 27. Round | 16/02/2020 | Rangers FC | - | Livingston FC | 1:0 | ||||
| 28. Round | 23/02/2020 | St. Johnstone FC | - | Rangers FC | 2:2 |
Scotland