| 1. Round | 26/01/2020 | Santiago Wanderers | - | Universidad Católica | 0:3 | ||||
| 2. Round | 01/02/2020 | Universidad de Concepción | - | Santiago Wanderers | 0:2 |  |
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| 3. Round | 10/02/2020 | O'Higgins | - | Santiago Wanderers | 2:1 | ||||
| 4. Round | 15/02/2020 | Santiago Wanderers | - | Universidad de Chile | 1:2 | |
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| 5. Round | 23/02/2020 | La Serena | - | Santiago Wanderers | 3:0 |  |
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| 27. Round | 02/01/2021 | Unión La Calera | - | Santiago Wanderers | 3:0 | ||||
| 28. Round | 06/01/2021 | Santiago Wanderers | - | Colo-Colo | 3:0 | ||||
| 30. Round | 16/01/2021 | Huachipato | - | Santiago Wanderers | 4:0 | ||||
| 32. Round | 06/02/2021 | Curicó Unido | - | Santiago Wanderers | 1:3 | |
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| 34. Round | 14/02/2021 | Deportes Iquique | - | Santiago Wanderers | 2:0 |
Argentina
Chile