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| 1st(1st leg) | Palestino | - | Deportes Concepción | 4:0 (2:0) | ||
| 2nd (2nd leg) | Deportes Concepción | - | Palestino | 0:4 (0:2) | ||
| 1st(1st leg): 30/06/2021 20:00 | 2nd (2nd leg): 03/07/2021 20:00 | Winner: Palestino | ||||
| 1st(1st leg) | Rangers | - | Coquimbo Unido | 0:1 (0:1) | ||
| 2nd (2nd leg) | Coquimbo Unido | - | Rangers | 0:0 (0:0) | ||
| 1st(1st leg): 30/06/2021 23:00 | 2nd (2nd leg): 04/07/2021 17:30 | Winner: Coquimbo Unido | ||||
| 1st(1st leg) | Everton | - | Universidad Católica | 0:0 (0:0) | ||
| 2nd (2nd leg) | Universidad Católica | - | Everton | 0:2 (0:2) | ||
| 1st(1st leg): 01/07/2021 01:30 | 2nd (2nd leg): 03/07/2021 20:00 | Winner: Everton | ||||
| 1st(1st leg) | Deportes Temuco | - | Huachipato | 2:2 (2:1) | ||
| 2nd (2nd leg) | Huachipato | - | Deportes Temuco | 2:0 (1:0) | ||
| 1st(1st leg): 01/07/2021 20:00 | 2nd (2nd leg): 05/07/2021 20:00 | Winner: Huachipato | ||||
| 1st(1st leg) | La Serena | - | Colo-Colo | 1:3 (1:1) | ||
| 2nd (2nd leg) | Colo-Colo | - | La Serena | 4:0 (1:0) | ||
| 1st(1st leg): 01/07/2021 20:30 | 2nd (2nd leg): 05/07/2021 01:00 | Winner: Colo-Colo | ||||
| 1st(1st leg) | Ñublense | - | O'Higgins | 1:1 (0:1) | ||
| 2nd (2nd leg) | O'Higgins | - | Ñublense | 2:3 (2:1, 2:2) pso | ||
| 1st(1st leg): 01/07/2021 23:00 | 2nd (2nd leg): 04/07/2021 22:30 | Winner: Ñublense | ||||
| 1st(1st leg) | Universidad de Chile | - | Fernández Vial | 1:1 (1:1) | ||
| 2nd (2nd leg) | Fernández Vial | - | Universidad de Chile | 5:4 (1:1, 1:1) pso | ||
| 1st(1st leg): 02/07/2021 01:30 | 2nd (2nd leg): 04/07/2021 20:00 | Winner: Fernández Vial | ||||
| 1st(1st leg) | CD Magallanes | - | Unión Española | 0:1 (0:0) | ||
| 2nd (2nd leg) | Unión Española | - | CD Magallanes | 1:0 (1:0) | ||
| 1st(1st leg): 09/07/2021 17:00 | 2nd (2nd leg): 12/07/2021 20:00 | Winner: Unión Española | ||||
