| 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 | ||||
| 24. Jornada | 04.10.2021 | Deportes Melipilla | - | Santiago Wanderers | 1:1 | ||||
| 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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| 27. Jornada | 20.10.2021 | Universidad Católica | - | Santiago Wanderers | 3:2 | |
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| 28. Jornada | 25.10.2021 | Santiago Wanderers | - | Antofagasta | 0:1 | ||||
| 29. Jornada | 29.10.2021 | Santiago Wanderers | - | Palestino | 1:1 | ||||
| 33. Jornada | 28.11.2021 | Santiago Wanderers | - | Audax Italiano | 2:2 | ||||
| 34. Jornada | 04.12.2021 | La Serena | - | Santiago Wanderers | 0:0 |
Argentina