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| 1st(1st leg) | Curicó Unido | - | Rangers | 1:1 (1:1) | ||
| 2nd (2nd leg) | Rangers | - | Curicó Unido | 3:2 (0:0, 1:1) pso | ||
| 1st(1st leg): 22/06/2021 01:30 | 2nd (2nd leg): 26/06/2021 01:30 | Winner: Rangers | ||||
| 1st(1st leg) | Antofagasta | - | Coquimbo Unido | 0:0 (0:0) | ||
| 2nd (2nd leg) | Coquimbo Unido | - | Antofagasta | 1:0 (0:0) | ||
| 1st(1st leg): 22/06/2021 17:30 | 2nd (2nd leg): 26/06/2021 17:00 | Winner: Coquimbo Unido | ||||
| 1st(1st leg) | Barnechea | - | Palestino | 0:2 (0:0) | ||
| 2nd (2nd leg) | Palestino | - | Barnechea | 5:2 (2:2) | ||
| 1st(1st leg): 22/06/2021 17:30 | 2nd (2nd leg): 27/06/2021 20:00 | Winner: Palestino | ||||
| 1st(1st leg) | Fernández Vial | - | Cobresal | 0:0 (0:0) | ||
| 2nd (2nd leg) | Cobresal | - | Fernández Vial | 2:4 (1:1, 2:2) pso | ||
| 1st(1st leg): 22/06/2021 23:00 | 2nd (2nd leg): 26/06/2021 16:00 | Winner: Fernández Vial | ||||
| 1st(1st leg) | Deportes Iquique | - | Universidad Católica | 1:1 (0:1) | ||
| 2nd (2nd leg) | Universidad Católica | - | Deportes Iquique | 9:8 (1:2, 4:4) pso | ||
| 1st(1st leg): 23/06/2021 01:00 | 2nd (2nd leg): 27/06/2021 01:30 | Winner: Universidad Católica | ||||
| 1st(1st leg) | Deportes Temuco | - | Unión La Calera | 0:0 (0:0) | ||
| 2nd (2nd leg) | Unión La Calera | - | Deportes Temuco | 0:2 (0:1) | ||
| 1st(1st leg): 23/06/2021 17:30 | 2nd (2nd leg): 26/06/2021 23:00 | Winner: Deportes Temuco | ||||
| 1st(1st leg) | Puerto Montt | - | Unión Española | 0:2 (0:1) | ||
| 2nd (2nd leg) | Unión Española | - | Puerto Montt | 2:3 (1:1) | ||
| 1st(1st leg): 23/06/2021 17:30 | 2nd (2nd leg): 27/06/2021 16:00 | Winner: Unión Española | ||||
| 1st(1st leg) | Melipilla | - | Ñublense | 0:1 (0:0) | ||
| 2nd (2nd leg) | Ñublense | - | Melipilla | 0:0 (0:0) | ||
| 1st(1st leg): 23/06/2021 20:30 | 2nd (2nd leg): 27/06/2021 20:00 | Winner: Ñublense | ||||
| 1st(1st leg) | Deportes Colina | - | La Serena | 1:2 (1:0) | ||
| 2nd (2nd leg) | La Serena | - | Deportes Colina | 5:0 (2:0) | ||
| 1st(1st leg): 23/06/2021 20:30 | 2nd (2nd leg): 27/06/2021 20:00 | Winner: La Serena | ||||
| 1st(1st leg) | San Antonio Unido | - | Huachipato | 0:0 (0:0) | ||
| 2nd (2nd leg) | Huachipato | - | San Antonio Unido | 3:2 (3:0) | ||
| 1st(1st leg): 23/06/2021 20:30 | 2nd (2nd leg): 26/06/2021 20:00 | Winner: Huachipato | ||||
| 1st(1st leg) | O'Higgins | - | Cobreloa | 1:0 (1:0) | ||
| 2nd (2nd leg) | Cobreloa | - | O'Higgins | 6:7 (0:1, 2:1, 2:1) pso | ||
| 1st(1st leg): 23/06/2021 22:30 | 2nd (2nd leg): 27/06/2021 17:00 | Winner: O'Higgins | ||||
| 1st(1st leg) | Everton | - | Santa Cruz | 3:0 (2:0) | ||
| 2nd (2nd leg) | Santa Cruz | - | Everton | 1:1 (0:0) | ||
| 1st(1st leg): 24/06/2021 01:00 | 2nd (2nd leg): 26/06/2021 23:00 | Winner: Everton | ||||
| 1st(1st leg) | Santiago Wanderers | - | Deportes Concepción | 0:1 (0:0) | ||
| 2nd (2nd leg) | Deportes Concepción | - | Santiago Wanderers | 1:1 (0:1) | ||
| 1st(1st leg): 24/06/2021 16:00 | 2nd (2nd leg): 27/06/2021 23:00 | Winner: Deportes Concepción | ||||
| 1st(1st leg) | Universidad de Chile | - | San Luis | 1:0 (0:0) | ||
| 2nd (2nd leg) | San Luis | - | Universidad de Chile | 1:3 (0:2) | ||
| 1st(1st leg): 24/06/2021 22:30 | 2nd (2nd leg): 28/06/2021 01:30 | Winner: Universidad de Chile | ||||
| 1st(1st leg) | CD Magallanes | - | Audax Italiano | 4:0 (1:0) | ||
| 2nd (2nd leg) | Audax Italiano | - | CD Magallanes | 3:0 (2:0) | ||
| 1st(1st leg): 30/06/2021 17:00 | 2nd (2nd leg): 05/07/2021 20:00 | Winner: CD Magallanes | ||||
