| 1. Round | 28/03/2021 | Unión Española | - | Santiago Wanderers | 3:1 |  |
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| 3. Round | 11/04/2021 | Santiago Wanderers | - | Unión La Calera | 1:2 | ||||
| 4. Round | 18/04/2021 | Cobresal | - | Santiago Wanderers | 2:1 | ||||
| 10. Round | 05/06/2021 | Santiago Wanderers | - | Universidad Católica | 0:1 | ||||
| 15. Round | 08/08/2021 | Santiago Wanderers | - | Huachipato | 1:4 | ||||
| 22. Round | 26/09/2021 | Ñublense | - | Santiago Wanderers | 1:2 |  |
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| 23. Round | 29/09/2021 | Santiago Wanderers | - | Universidad de Chile | 2:1 | ||||
| 25. Round | 11/10/2021 | O'Higgins | - | Santiago Wanderers | 1:0 | ||||
| 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 | ||||
| 34. Round | 04/12/2021 | La Serena | - | Santiago Wanderers | 0:0 |
Brazil