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| H | Curicó Unido | - | Rangers | 1:1 (1:1) | ||
| R | Rangers | - | Curicó Unido | 3:2 (0:0, 1:1) i.E. | ||
| H: 22.06.2021 02:30 | R: 26.06.2021 02:30 | Sieger: Rangers | ||||
| H | Antofagasta | - | Coquimbo Unido | 0:0 (0:0) | ||
| R | Coquimbo Unido | - | Antofagasta | 1:0 (0:0) | ||
| H: 22.06.2021 18:30 | R: 26.06.2021 18:00 | Sieger: Coquimbo Unido | ||||
| H | Barnechea | - | Palestino | 0:2 (0:0) | ||
| R | Palestino | - | Barnechea | 5:2 (2:2) | ||
| H: 22.06.2021 18:30 | R: 27.06.2021 21:00 | Sieger: Palestino | ||||
| H | Fernández Vial | - | Cobresal | 0:0 (0:0) | ||
| R | Cobresal | - | Fernández Vial | 2:4 (1:1, 2:2) i.E. | ||
| H: 23.06.2021 00:00 | R: 26.06.2021 17:00 | Sieger: Fernández Vial | ||||
| H | Deportes Iquique | - | Universidad Católica | 1:1 (0:1) | ||
| R | Universidad Católica | - | Deportes Iquique | 9:8 (1:2, 4:4) i.E. | ||
| H: 23.06.2021 02:00 | R: 27.06.2021 02:30 | Sieger: Universidad Católica | ||||
| H | Deportes Temuco | - | Unión La Calera | 0:0 (0:0) | ||
| R | Unión La Calera | - | Deportes Temuco | 0:2 (0:1) | ||
| H: 23.06.2021 18:30 | R: 27.06.2021 00:00 | Sieger: Deportes Temuco | ||||
| H | Puerto Montt | - | Unión Española | 0:2 (0:1) | ||
| R | Unión Española | - | Puerto Montt | 2:3 (1:1) | ||
| H: 23.06.2021 18:30 | R: 27.06.2021 17:00 | Sieger: Unión Española | ||||
| H | Melipilla | - | Ñublense | 0:1 (0:0) | ||
| R | Ñublense | - | Melipilla | 0:0 (0:0) | ||
| H: 23.06.2021 21:30 | R: 27.06.2021 21:00 | Sieger: Ñublense | ||||
| H | Deportes Colina | - | La Serena | 1:2 (1:0) | ||
| R | La Serena | - | Deportes Colina | 5:0 (2:0) | ||
| H: 23.06.2021 21:30 | R: 27.06.2021 21:00 | Sieger: La Serena | ||||
| H | San Antonio Unido | - | Huachipato | 0:0 (0:0) | ||
| R | Huachipato | - | San Antonio Unido | 3:2 (3:0) | ||
| H: 23.06.2021 21:30 | R: 26.06.2021 21:00 | Sieger: Huachipato | ||||
| H | O'Higgins | - | Cobreloa | 1:0 (1:0) | ||
| R | Cobreloa | - | O'Higgins | 6:7 (0:1, 2:1, 2:1) i.E. | ||
| H: 23.06.2021 23:30 | R: 27.06.2021 18:00 | Sieger: O'Higgins | ||||
| H | Everton | - | Santa Cruz | 3:0 (2:0) | ||
| R | Santa Cruz | - | Everton | 1:1 (0:0) | ||
| H: 24.06.2021 02:00 | R: 27.06.2021 00:00 | Sieger: Everton | ||||
| H | Santiago Wanderers | - | Deportes Concepción | 0:1 (0:0) | ||
| R | Deportes Concepción | - | Santiago Wanderers | 1:1 (0:1) | ||
| H: 24.06.2021 17:00 | R: 28.06.2021 00:00 | Sieger: Deportes Concepción | ||||
| H | Universidad de Chile | - | San Luis | 1:0 (0:0) | ||
| R | San Luis | - | Universidad de Chile | 1:3 (0:2) | ||
| H: 24.06.2021 23:30 | R: 28.06.2021 02:30 | Sieger: Universidad de Chile | ||||
| H | CD Magallanes | - | Audax Italiano | 4:0 (1:0) | ||
| R | Audax Italiano | - | CD Magallanes | 3:0 (2:0) | ||
| H: 30.06.2021 18:00 | R: 05.07.2021 21:00 | Sieger: CD Magallanes | ||||
