| 1. Jornada | 15.05.2021 | Montevideo Wanderers | - | Boston River | 1:0 |  |
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| 2. Jornada | 22.05.2021 | Boston River | - | Rentistas | 1:2 | ||||
| 3. Jornada | 30.05.2021 | Peñarol | - | Boston River | 5:2 |  |
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| 4. Jornada | 06.06.2021 | Boston River | - | Montevideo City Torque | 1:2 | ||||
| 5. Jornada | 14.06.2021 | Villa Española | - | Boston River | 2:2 | ||||
| 6. Jornada | 19.06.2021 | Boston River | - | Nacional | 1:1 | ||||
| 7. Jornada | 23.06.2021 | Cerrito | - | Boston River | 1:0 | ||||
| 8. Jornada | 27.06.2021 | Boston River | - | Liverpool | 1:1 | ||||
| 9. Jornada | 03.07.2021 | River Plate | - | Boston River | 1:1 | |
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| 10. Jornada | 11.07.2021 | Boston River | - | Cerro Largo | 1:0 | ||||
| 11. Jornada | 16.07.2021 | Progreso | - | Boston River | 1:0 | |
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| 12. Jornada | 31.07.2021 | Boston River | - | Sud América | 2:0 | ||||
| 13. Jornada | 09.08.2021 | Plaza Colonia | - | Boston River | 0:0 | ||||
| 14. Jornada | 16.08.2021 | Boston River | - | Fénix | 0:2 | |
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