| 1. Round | 07/04/2021 | Rangers | - | Unión San Felipe | 3:1 | ||||
| 2. Round | 17/04/2021 | Unión San Felipe | - | Puerto Montt | 2:3 |  |
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| 3. Round | 26/04/2021 | Deportes Temuco | - | Unión San Felipe | 3:0 | ||||
| 4. Round | 03/05/2021 | San Luis | - | Unión San Felipe | 1:2 |  |
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| 5. Round | 10/05/2021 | Unión San Felipe | - | Cobreloa | 0:0 | ||||
| 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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| 9. Round | 06/06/2021 | Unión San Felipe | - | Barnechea | 2:4 | ||||
| 11. Round | 15/07/2021 | Unión San Felipe | - | Deportes Iquique | 3:1 | ||||
| 12. Round | 22/07/2021 | Deportes Copiapó | - | Unión San Felipe | 1:0 | ||||
| 28. Round | 01/11/2021 | Santiago Morning | - | Unión San Felipe | 1:0 | ||||
| 29. Round | 09/11/2021 | Coquimbo Unido | - | Unión San Felipe | 4:1 | ||||
| 30. Round | 13/11/2021 | Unión San Felipe | - | CD Magallanes | 0:0 |
Chile