| 1. Round | 07/04/2021 | Rangers | - | Unión San Felipe | 3:1 | ||||
| 3. Round | 26/04/2021 | Deportes Temuco | - | Unión San Felipe | 3:0 | ||||
| 4. Round | 03/05/2021 | San Luis | - | Unión San Felipe | 1:2 | ||||
| 5. Round | 10/05/2021 | Unión San Felipe | - | Cobreloa | 0:0 | ||||
| 6. Round | 18/05/2021 | Universidad de Concepción | - | Unión San Felipe | 0:0 | ||||
| 11. Round | 15/07/2021 | Unión San Felipe | - | Deportes Iquique | 3:1 |  |
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| 12. Round | 22/07/2021 | Deportes Copiapó | - | Unión San Felipe | 1:0 | ||||
| 14. Round | 09/08/2021 | Unión San Felipe | - | Coquimbo Unido | 1:1 | ||||
| 19. Round | 07/09/2021 | Unión San Felipe | - | San Luis | 1:1 |  |
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| 20. Round | 16/09/2021 | Cobreloa | - | Unión San Felipe | 2:1 | ||||
| 21. Round | 23/09/2021 | Unión San Felipe | - | Universidad de Concepción | 1:0 | ||||
| 22. Round | 28/09/2021 | Santa Cruz | - | Unión San Felipe | 0:1 | |
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| 23. Round | 03/10/2021 | Unión San Felipe | - | San Marcos | 0:0 | |
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| 24. Round | 10/10/2021 | Barnechea | - | Unión San Felipe | 2:4 | |
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| 25. Round | 13/10/2021 | Unión San Felipe | - | Fernández Vial | 0:1 | |
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| 26. Round | 20/10/2021 | Deportes Iquique | - | Unión San Felipe | 1:0 | ||||
| 30. Round | 13/11/2021 | Unión San Felipe | - | CD Magallanes | 0:0 |
Chile