| 1. Round | 25/02/2020 | Rangers | - | Unión San Felipe | 2:2 |  |
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| 2. Round | 01/03/2020 | Unión San Felipe | - | Deportes Copiapó | 2:1 | |
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| 3. Round | 10/03/2020 | Deportes Valdivia | - | Unión San Felipe | 2:2 | |
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| 4. Round | 17/03/2020 | Unión San Felipe | - | Santa Cruz | 1:1 | ||||
| 6. Round | 05/09/2020 | Deportes Melipilla | - | Unión San Felipe | 0:1 | |
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| 7. Round | 08/09/2020 | Unión San Felipe | - | Deportes Temuco | 1:1 | |
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| 8. Round | 13/09/2020 | Puerto Montt | - | Unión San Felipe | 1:0 | ||||
| 9. Round | 17/09/2020 | Unión San Felipe | - | Ñublense | 0:0 | ||||
| 10. Round | 23/09/2020 | Cobreloa | - | Unión San Felipe | 0:2 | ||||
| 11. Round | 27/09/2020 | Unión San Felipe | - | San Luis | 2:1 | ||||
| 12. Round | 01/10/2020 | Santiago Morning | - | Unión San Felipe | 0:4 | |
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| 13. Round | 05/10/2020 | Unión San Felipe | - | San Marcos | 1:0 | ||||
| 14. Round | 09/10/2020 | Barnechea | - | Unión San Felipe | 1:0 | ||||
| 15. Round | 13/10/2020 | Unión San Felipe | - | CD Magallanes | 1:2 | ||||
| 16. Round | 27/10/2020 | Unión San Felipe | - | San Luis | 1:1 | ||||
| 17. Round | 04/11/2020 | Santa Cruz | - | Unión San Felipe | 2:1 |
Chile