| 1. Round | 28/03/2021 | Unión Española | - | Santiago Wanderers | 3:1 | ||||
| 6. Round | 04/05/2021 | Universidad de Chile | - | Santiago Wanderers | 1:0 | ||||
| 7. Round | 08/05/2021 | Santiago Wanderers | - | Deportes Melipilla | 0:3 | ||||
| 8. Round | 22/05/2021 | Santiago Wanderers | - | O'Higgins | 0:0 |  |
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| 11. Round | 16/07/2021 | Antofagasta | - | Santiago Wanderers | 1:0 | ||||
| 12. Round | 25/07/2021 | Palestino | - | Santiago Wanderers | 2:0 | ||||
| 13. Round | 29/07/2021 | Santiago Wanderers | - | Colo-Colo | 0:4 | ||||
| 14. Round | 03/08/2021 | Curicó Unido | - | Santiago Wanderers | 2:1 | ||||
| 15. Round | 08/08/2021 | Santiago Wanderers | - | Huachipato | 1:4 |  |
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| 16. Round | 14/08/2021 | Audax Italiano | - | Santiago Wanderers | 1:0 | ||||
| 20. Round | 08/09/2021 | Unión La Calera | - | Santiago Wanderers | 0:1 | ||||
| 21. Round | 12/09/2021 | Santiago Wanderers | - | Cobresal | 2:1 | |
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| 30. Round | 06/11/2021 | Colo-Colo | - | Santiago Wanderers | 3:0 | ||||
| 32. Round | 15/11/2021 | Huachipato | - | Santiago Wanderers | 2:0 | ||||
| 33. Round | 28/11/2021 | Santiago Wanderers | - | Audax Italiano | 2:2 |
Chile