| 3. Jornada | 22.09.2019 | River Plate | - | Boston River | 1:4 | ||||
| 9. Jornada | 02.11.2019 | Rampla Juniors | - | Boston River | 0:1 |  |
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| 10. Jornada | 06.11.2019 | Boston River | - | Juventud de Las Piedras | 2:1 | |
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| 11. Jornada | 10.11.2019 | Liverpool | - | Boston River | 0:0 | |
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| 12. Jornada | 16.11.2019 | Boston River | - | Montevideo Wanderers | 1:3 | |
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| 13. Jornada | 22.11.2019 | Racing | - | Boston River | 0:1 | ||||
| 14. Jornada | 27.11.2019 | Cerro Largo | - | Boston River | 1:0 | ||||
| 15. Jornada | 05.12.2019 | Boston River | - | Danubio | 3:1 | |
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