| 1. Round | 28/03/2021 | Unión Española | - | Santiago Wanderers | 3:1 | ||||
| 3. Round | 11/04/2021 | Santiago Wanderers | - | Unión La Calera | 1:2 | ||||
| 4. Round | 18/04/2021 | Cobresal | - | Santiago Wanderers | 2:1 |  |
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| 5. Round | 25/04/2021 | Santiago Wanderers | - | Ñublense | 1:2 | ||||
| 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 | ||||
| 9. Round | 30/05/2021 | Everton | - | Santiago Wanderers | 1:0 | ||||
| 10. Round | 05/06/2021 | Santiago Wanderers | - | Universidad Católica | 0:1 | ||||
| 11. Round | 16/07/2021 | Antofagasta | - | Santiago Wanderers | 1:0 |  |
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| 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 | ||||
| 17. Round | 21/08/2021 | Santiago Wanderers | - | La Serena | 2:2 |
Chile