| 1. Jornada | 28.03.2021 | Unión Española | - | Santiago Wanderers | 3:1 |  |
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| 3. Jornada | 11.04.2021 | Santiago Wanderers | - | Unión La Calera | 1:2 | ||||
| 4. Jornada | 18.04.2021 | Cobresal | - | Santiago Wanderers | 2:1 | ||||
| 10. Jornada | 05.06.2021 | Santiago Wanderers | - | Universidad Católica | 0:1 | ||||
| 15. Jornada | 08.08.2021 | Santiago Wanderers | - | Huachipato | 1:4 | ||||
| 22. Jornada | 26.09.2021 | Ñublense | - | Santiago Wanderers | 1:2 |  |
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| 23. Jornada | 29.09.2021 | Santiago Wanderers | - | Universidad de Chile | 2:1 | ||||
| 25. Jornada | 11.10.2021 | O'Higgins | - | Santiago Wanderers | 1:0 | ||||
| 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 | ||||
| 34. Jornada | 04.12.2021 | La Serena | - | Santiago Wanderers | 0:0 |
Brasil