| 1. Round | 07/04/2021 | Rangers | - | Unión San Felipe | 3:1 |  |
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| 2. Round | 17/04/2021 | Unión San Felipe | - | Puerto Montt | 2:3 | ||||
| 3. Round | 26/04/2021 | Deportes Temuco | - | Unión San Felipe | 3:0 | ||||
| 4. Round | 03/05/2021 | San Luis | - | Unión San Felipe | 1:2 | ||||
| 8. Round | 01/06/2021 | San Marcos | - | Unión San Felipe | 3:1 | ||||
| 24. Round | 10/10/2021 | Barnechea | - | Unión San Felipe | 2:4 | ||||
| 25. Round | 13/10/2021 | Unión San Felipe | - | Fernández Vial | 0:1 | ||||
| 26. Round | 20/10/2021 | Deportes Iquique | - | Unión San Felipe | 1:0 | ||||
| 27. Round | 24/10/2021 | Unión San Felipe | - | Deportes Copiapó | 2:3 | |
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| 10. Round | 29/10/2021 | Fernández Vial | - | Unión San Felipe | 1:3 | ||||
| 28. Round | 01/11/2021 | Santiago Morning | - | Unión San Felipe | 1:0 | ||||
| 29. Round | 09/11/2021 | Coquimbo Unido | - | Unión San Felipe | 4:1 |  |
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| 30. Round | 13/11/2021 | Unión San Felipe | - | CD Magallanes | 0:0 |
Chile