| 4. Round | 03/05/2021 | San Luis | - | Unión San Felipe | 1:2 | ||||
| 6. Round | 18/05/2021 | Universidad de Concepción | - | Unión San Felipe | 0:0 | ||||
| 7. Round | 25/05/2021 | Unión San Felipe | - | Santa Cruz | 1:0 |  |
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| 8. Round | 01/06/2021 | San Marcos | - | Unión San Felipe | 3:1 | ||||
| 9. Round | 06/06/2021 | Unión San Felipe | - | Barnechea | 2:4 | ||||
| 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 | |
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| 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 | ||||
| 10. Round | 29/10/2021 | Fernández Vial | - | Unión San Felipe | 1:3 |
Chile