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| 15/06/2021 | 20:00 | Cobreloa | - | Copiapó | 2:1 (0:1) | |
| 20:00 | Colchagua | - | Santa Cruz | 1:6 (0:3) | ||
| 20:00 | Deportes Valdivia | - | Puerto Montt | 1:3 (0:1) | ||
| 20:00 | Deportes Iberia | - | Deportes Temuco | 0:1 (0:1) | ||
| 20:00 | Rodelindo Román | - | Coquimbo Unido | 0:1 (0:0) | ||
| 20:00 | Limache | - | Barnechea | 1:4 (1:2) | ||
| 20:00 | Deportes Colina | - | Santiago Morning | 1:0 (1:0) | ||
| 20:00 | General Velásquez | - | Rangers | 0:1 (0:0) | ||
| 20:00 | Recoleta | - | San Luis | 0:3 (2:1, 3:1) dec. | ||
| 20:00 | Independiente | - | Fernández Vial | 1:3 (0:0) | ||
| 23:00 | Deportes Concepción | - | Universidad de Concepción | 1:0 (0:0) | ||
| 16/06/2021 | 01:00 | Deportes Iquique | - | San Marcos | 4:3 (1:1, 2:2, 2:2) pso | |
| 20:00 | CSD Lautaro | - | CD Magallanes | 2:4 (1:1, 1:1) pso | ||
| 20:00 | San Antonio Unido | - | Unión San Felipe | 2:0 (0:0) |
