| 2. Round | 20/09/2019 | Montevideo Wanderers | - | Nacional | 0:1 |  |
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| 3. Round | 22/09/2019 | Fénix | - | Montevideo Wanderers | 3:3 | ||||
| 4. Round | 05/10/2019 | Montevideo Wanderers | - | Progreso | 0:1 | ||||
| 5. Round | 11/10/2019 | Peñarol | - | Montevideo Wanderers | 1:0 | ||||
| 6. Round | 17/10/2019 | Montevideo Wanderers | - | Defensor Sporting | 2:0 | ||||
| 7. Round | 20/10/2019 | Rampla Juniors | - | Montevideo Wanderers | 1:1 | ||||
| 8. Round | 25/10/2019 | Montevideo Wanderers | - | Juventud de Las Piedras | 3:0 | ||||
| 9. Round | 03/11/2019 | Liverpool | - | Montevideo Wanderers | 2:2 | ||||
| 10. Round | 07/11/2019 | Cerro Largo | - | Montevideo Wanderers | 0:2 | |
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| 12. Round | 16/11/2019 | Boston River | - | Montevideo Wanderers | 1:3 | ||||
| 13. Round | 21/11/2019 | Montevideo Wanderers | - | Danubio | 2:1 | ||||
| 14. Round | 27/11/2019 | Plaza Colonia | - | Montevideo Wanderers | 0:0 | |
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| 15. Round | 05/12/2019 | Montevideo Wanderers | - | CA Cerro | 0:2 | |
Uruguay