| 1. Round | 15/09/2019 | Progreso | - | Rampla Juniors | 2:2 |  |
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| 2. Round | 18/09/2019 | Juventud de Las Piedras | - | Progreso | 1:2 | ||||
| 3. Round | 22/09/2019 | Progreso | - | Liverpool | 2:1 | |
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| 4. Round | 05/10/2019 | Montevideo Wanderers | - | Progreso | 0:1 | |
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| 5. Round | 09/10/2019 | Progreso | - | Racing | 2:1 | ||||
| 6. Round | 16/10/2019 | Boston River | - | Progreso | 1:1 | ||||
| 7. Round | 19/10/2019 | Progreso | - | Danubio | 2:1 | |
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| 8. Round | 24/10/2019 | Plaza Colonia | - | Progreso | 0:1 |  |
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| 9. Round | 03/11/2019 | Progreso | - | CA Cerro | 1:1 | ||||
| 10. Round | 06/11/2019 | River Plate | - | Progreso | 1:2 | ||||
| 11. Round | 10/11/2019 | Progreso | - | Nacional | 0:1 | ||||
| 12. Round | 16/11/2019 | Fénix | - | Progreso | 1:2 | ||||
| 13. Round | 21/11/2019 | Progreso | - | Cerro Largo | 0:1 | ||||
| 14. Round | 27/11/2019 | Progreso | - | Peñarol | 0:0 | ||||
| 15. Round | 05/12/2019 | Defensor Sporting | - | Progreso | 2:4 | |
Uruguay