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| 1st(1st leg) | Cobresal | - | Universidad de Chile | 3:1 (2:1) | ||
| 2nd (2nd leg) | Universidad de Chile | - | Cobresal | 4:1 (2:0) | ||
| 1st(1st leg): 07/09/2019 20:00 | 2nd (2nd leg): 12/10/2019 00:00 | Winner: Universidad de Chile | ||||
| 1st(1st leg) | Colo-Colo | - | Everton | 2:1 (0:1) | ||
| 2nd (2nd leg) | Everton | - | Colo-Colo | 1:2 (1:0) | ||
| 1st(1st leg): 07/09/2019 22:30 | 2nd (2nd leg): 12/10/2019 19:15 | Winner: Colo-Colo | ||||
| 1st(1st leg) | Unión La Calera | - | Universidad Católica | 2:1 (2:1) | ||
| 2nd (2nd leg) | Universidad Católica | - | Unión La Calera | 2:0 (1:0) | ||
| 1st(1st leg): 08/09/2019 19:00 | 2nd (2nd leg): 13/10/2019 00:15 | Winner: Universidad Católica | ||||
| 1st(1st leg) | Audax Italiano | - | Unión Española | 0:1 (0:1) | ||
| 2nd (2nd leg) | Unión Española | - | Audax Italiano | 2:1 (1:1) | ||
| 1st(1st leg): 08/09/2019 21:30 | 2nd (2nd leg): 12/10/2019 21:45 | Winner: Unión Española | ||||
