| 8. Round | 01/06/2021 | San Marcos | - | Unión San Felipe | 3:1 | ||||
| 9. Round | 06/06/2021 | Unión San Felipe | - | Barnechea | 2:4 | ||||
| 12. Round | 22/07/2021 | Deportes Copiapó | - | Unión San Felipe | 1:0 | ||||
| 13. Round | 31/07/2021 | Unión San Felipe | - | Santiago Morning | 0:2 |  |
|||
| 14. Round | 09/08/2021 | Unión San Felipe | - | Coquimbo Unido | 1:1 | |
|||
| 15. Round | 16/08/2021 | CD Magallanes | - | Unión San Felipe | 2:1 | |
|||
| 16. Round | 23/08/2021 | Unión San Felipe | - | Rangers | 2:1 | ||||
| 17. Round | 28/08/2021 | Puerto Montt | - | Unión San Felipe | 0:1 | ||||
| 18. Round | 01/09/2021 | Unión San Felipe | - | Deportes Temuco | 1:2 | ||||
| 19. Round | 07/09/2021 | Unión San Felipe | - | San Luis | 1:1 | ||||
| 20. Round | 16/09/2021 | Cobreloa | - | Unión San Felipe | 2:1 | |
|||
| 21. Round | 23/09/2021 | Unión San Felipe | - | Universidad de Concepción | 1:0 |
Chile