| 1. Round | 04/04/2021 | Cobreloa | - | Barnechea | 1:2 | ||||
| 5. Round | 10/05/2021 | Unión San Felipe | - | Cobreloa | 0:0 |  |
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| 6. Round | 18/05/2021 | Cobreloa | - | Santiago Morning | 2:2 | |
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| 8. Round | 30/05/2021 | Cobreloa | - | San Luis | 1:0 | ||||
| 10. Round | 09/07/2021 | Cobreloa | - | Deportes Iquique | 3:2 | ||||
| 17. Round | 29/08/2021 | Cobreloa | - | San Marcos | 0:3 dec. | |
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| 18. Round | 02/09/2021 | Universidad de Concepción | - | Cobreloa | 0:0 | ||||
| 19. Round | 06/09/2021 | Coquimbo Unido | - | Cobreloa | 2:1 | ||||
| 20. Round | 16/09/2021 | Cobreloa | - | Unión San Felipe | 2:1 | ||||
| 21. Round | 22/09/2021 | Santiago Morning | - | Cobreloa | 2:1 | ||||
| 22. Round | 26/09/2021 | Cobreloa | - | Fernández Vial | 1:2 | ||||
| 23. Round | 02/10/2021 | San Luis | - | Cobreloa | 1:0 | ||||
| 25. Round | 13/10/2021 | Deportes Iquique | - | Cobreloa | 1:0 | ||||
| 26. Round | 16/10/2021 | Cobreloa | - | Copiapó | 2:0 | ||||
| 27. Round | 28/10/2021 | Puerto Montt | - | Cobreloa | 0:0 | |
Chile