| 3. Ronde | 11.04.2021 | Santiago Wanderers | - | Unión La Calera | 1:2 | ||||
| 4. Ronde | 18.04.2021 | Cobresal | - | Santiago Wanderers | 2:1 | ||||
| 5. Ronde | 25.04.2021 | Santiago Wanderers | - | Ñublense | 1:2 | ||||
| 6. Ronde | 04.05.2021 | Universidad de Chile | - | Santiago Wanderers | 1:0 | ||||
| 7. Ronde | 09.05.2021 | Santiago Wanderers | - | Deportes Melipilla | 0:3 | ||||
| 8. Ronde | 23.05.2021 | Santiago Wanderers | - | O'Higgins | 0:0 | ||||
| 9. Ronde | 30.05.2021 | Everton | - | Santiago Wanderers | 1:0 |  |
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| 10. Ronde | 05.06.2021 | Santiago Wanderers | - | Universidad Católica | 0:1 | ||||
| 11. Ronde | 16.07.2021 | Antofagasta | - | Santiago Wanderers | 1:0 | |
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| 12. Ronde | 25.07.2021 | Palestino | - | Santiago Wanderers | 2:0 | ||||
| 13. Ronde | 29.07.2021 | Santiago Wanderers | - | Colo-Colo | 0:4 | ||||
| 14. Ronde | 03.08.2021 | Curicó Unido | - | Santiago Wanderers | 2:1 |
Uruguay