| 1. Round | 15/09/2019 | Plaza Colonia | - | Boston River | 1:0 | ||||
| 2. Round | 19/09/2019 | Boston River | - | CA Cerro | 2:2 | ||||
| 3. Round | 22/09/2019 | River Plate | - | Boston River | 1:4 |  |
|||
| 4. Round | 05/10/2019 | Boston River | - | Nacional | 0:2 | ||||
| 5. Round | 09/10/2019 | Fénix | - | Boston River | 1:2 | ||||
| 6. Round | 16/10/2019 | Boston River | - | Progreso | 1:1 | |
|||
| 7. Round | 20/10/2019 | Peñarol | - | Boston River | 1:0 | ||||
| 8. Round | 25/10/2019 | Boston River | - | Defensor Sporting | 1:4 | ||||
| 9. Round | 02/11/2019 | Rampla Juniors | - | Boston River | 0:1 | ||||
| 10. Round | 06/11/2019 | Boston River | - | Juventud de Las Piedras | 2:1 | |
|||
| 11. Round | 10/11/2019 | Liverpool | - | Boston River | 0:0 |  |
|||
| 12. Round | 16/11/2019 | Boston River | - | Montevideo Wanderers | 1:3 | |
|||
| 13. Round | 22/11/2019 | Racing | - | Boston River | 0:1 | ||||
| 14. Round | 27/11/2019 | Cerro Largo | - | Boston River | 1:0 | ||||
| 15. Round | 05/12/2019 | Boston River | - | Danubio | 3:1 | |
|
Uruguay