| 5. Jornada | 25.04.2021 | Santiago Wanderers | - | Ñublense | 1:2 | ||||
| 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 | ||||
| 15. Jornada | 08.08.2021 | Santiago Wanderers | - | Huachipato | 1:4 | ||||
| 16. Jornada | 14.08.2021 | Audax Italiano | - | Santiago Wanderers | 1:0 | ||||
| 17. Jornada | 21.08.2021 | Santiago Wanderers | - | La Serena | 2:2 |  |
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| 18. Jornada | 26.08.2021 | Santiago Wanderers | - | Unión Española | 1:2 | |
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| 24. Jornada | 04.10.2021 | Deportes Melipilla | - | Santiago Wanderers | 1:1 | |
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| 25. Jornada | 11.10.2021 | O'Higgins | - | Santiago Wanderers | 1:0 | ||||
| 26. Jornada | 16.10.2021 | Santiago Wanderers | - | Everton | 2:1 |  |
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| 28. Jornada | 25.10.2021 | Santiago Wanderers | - | Antofagasta | 0:1 | |
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| 29. Jornada | 29.10.2021 | Santiago Wanderers | - | Palestino | 1:1 | ||||
| 30. Jornada | 06.11.2021 | Colo-Colo | - | Santiago Wanderers | 3:0 |
Chile