| 10. Round | 08/09/2020 | Unión Española | - | Santiago Wanderers | 2:1 | ||||
| 11. Round | 13/09/2020 | Santiago Wanderers | - | Huachipato | 3:2 | ||||
| 12. Round | 25/09/2020 | Coquimbo Unido | - | Santiago Wanderers | 2:1 | ||||
| 13. Round | 02/10/2020 | Santiago Wanderers | - | Deportes Iquique | 3:1 | ||||
| 14. Round | 10/10/2020 | Everton | - | Santiago Wanderers | 2:2 | ||||
| 24. Round | 16/12/2020 | Palestino | - | Santiago Wanderers | 3:1 | ||||
| 22. Round | 30/12/2020 | Universidad Católica | - | Santiago Wanderers | 1:1 | ||||
| 27. Round | 02/01/2021 | Unión La Calera | - | Santiago Wanderers | 3:0 | ||||
| 29. Round | 11/01/2021 | Santiago Wanderers | - | Cobresal | 1:0 | ||||
| 30. Round | 16/01/2021 | Huachipato | - | Santiago Wanderers | 4:0 | ||||
| 31. Round | 18/01/2021 | Santiago Wanderers | - | La Serena | 0:0 | ||||
| 33. Round | 11/02/2021 | Santiago Wanderers | - | Universidad de Concepción | 1:1 | ||||
| 34. Round | 14/02/2021 | Deportes Iquique | - | Santiago Wanderers | 2:0 |
Brazil