| 10. Jornada | 08.09.2020 | Unión Española | - | Santiago Wanderers | 2:1 | ||||
| 13. Jornada | 02.10.2020 | Santiago Wanderers | - | Deportes Iquique | 3:1 |  |
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| 17. Jornada | 29.10.2020 | Cobresal | - | Santiago Wanderers | 1:0 | ||||
| 25. Jornada | 20.12.2020 | Antofagasta | - | Santiago Wanderers | 1:1 | ||||
| 26. Jornada | 27.12.2020 | Santiago Wanderers | - | O'Higgins | 1:0 | ||||
| 22. Jornada | 31.12.2020 | Universidad Católica | - | Santiago Wanderers | 1:1 | ||||
| 27. Jornada | 02.01.2021 | Unión La Calera | - | Santiago Wanderers | 3:0 | ||||
| 32. Jornada | 06.02.2021 | Curicó Unido | - | Santiago Wanderers | 1:3 |
Chile