| 3. Jornada | 11.04.2021 | Santiago Wanderers | - | Unión La Calera | 1:2 | ||||
| 4. Jornada | 18.04.2021 | Cobresal | - | Santiago Wanderers | 2:1 |  |
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| 5. Jornada | 25.04.2021 | Santiago Wanderers | - | Ñublense | 1:2 | |
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| 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 | ||||
| 9. Jornada | 30.05.2021 | Everton | - | Santiago Wanderers | 1:0 | |
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| 10. Jornada | 05.06.2021 | Santiago Wanderers | - | Universidad Católica | 0:1 | |
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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 | |
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| 17. Jornada | 21.08.2021 | Santiago Wanderers | - | La Serena | 2:2 | ||||
| 18. Jornada | 26.08.2021 | Santiago Wanderers | - | Unión Española | 1:2 | |
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| 20. Jornada | 08.09.2021 | Unión La Calera | - | Santiago Wanderers | 0:1 |  |
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| 21. Jornada | 12.09.2021 | Santiago Wanderers | - | Cobresal | 2:1 |
Chile