| 1. Jornada | 28.03.2021 | Unión Española | - | Santiago Wanderers | 3:1 | ||||
| 6. Jornada | 04.05.2021 | Universidad de Chile | - | Santiago Wanderers | 1:0 | ||||
| 7. Jornada | 09.05.2021 | Santiago Wanderers | - | Deportes Melipilla | 0:3 | ||||
| 8. Jornada | 23.05.2021 | Santiago Wanderers | - | O'Higgins | 0:0 |  |
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| 11. Jornada | 16.07.2021 | Antofagasta | - | Santiago Wanderers | 1:0 | ||||
| 12. Jornada | 25.07.2021 | Palestino | - | Santiago Wanderers | 2:0 | ||||
| 13. Jornada | 29.07.2021 | Santiago Wanderers | - | Colo-Colo | 0:4 | ||||
| 14. Jornada | 03.08.2021 | Curicó Unido | - | Santiago Wanderers | 2:1 | ||||
| 15. Jornada | 08.08.2021 | Santiago Wanderers | - | Huachipato | 1:4 |  |
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| 16. Jornada | 14.08.2021 | Audax Italiano | - | Santiago Wanderers | 1:0 | ||||
| 20. Jornada | 08.09.2021 | Unión La Calera | - | Santiago Wanderers | 0:1 | ||||
| 21. Jornada | 12.09.2021 | Santiago Wanderers | - | Cobresal | 2:1 | |
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| 30. Jornada | 06.11.2021 | Colo-Colo | - | Santiago Wanderers | 3:0 | ||||
| 32. Jornada | 15.11.2021 | Huachipato | - | Santiago Wanderers | 2:0 | ||||
| 33. Jornada | 28.11.2021 | Santiago Wanderers | - | Audax Italiano | 2:2 |
Chile