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| 1st(1st leg) | Palestino | - | Colo-Colo | 2:3 (0:1) | ||
| 2nd (2nd leg) | Colo-Colo | - | Palestino | 1:1 (0:1) | ||
| 1st(1st leg): 08/07/2021 20:00 | 2nd (2nd leg): 12/07/2021 01:30 | Winner: Colo-Colo | ||||
| 1st(1st leg) | Everton | - | Ñublense | 1:0 (1:0) | ||
| 2nd (2nd leg) | Ñublense | - | Everton | 1:1 (1:0) | ||
| 1st(1st leg): 09/07/2021 01:30 | 2nd (2nd leg): 11/07/2021 23:00 | Winner: Everton | ||||
| 1st(1st leg) | Fernández Vial | - | Coquimbo Unido | 0:0 (0:0) | ||
| 2nd (2nd leg) | Coquimbo Unido | - | Fernández Vial | 3:0 (2:0) | ||
| 1st(1st leg): 10/07/2021 21:30 | 2nd (2nd leg): 06/08/2021 01:00 | Winner: Coquimbo Unido | ||||
| 1st(1st leg) | Unión Española | - | Huachipato | 1:1 (0:1) | ||
| 2nd (2nd leg) | Huachipato | - | Unión Española | 0:1 (0:0) | ||
| 1st(1st leg): 05/08/2021 01:00 | 2nd (2nd leg): 12/08/2021 01:00 | Winner: Unión Española | ||||
