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| 1st(1st leg) | Unión Española | - | Deportes Valdivia | 0:0 (0:0) | ||
| 2nd (2nd leg) | Deportes Valdivia | - | Unión Española | 0:2 (0:0) | ||
| 1st(1st leg): 13/07/2019 22:30 | 2nd (2nd leg): 05/09/2019 00:00 | Winner: Unión Española | ||||
| 1st(1st leg) | Everton | - | O'Higgins | 1:0 (0:0) | ||
| 2nd (2nd leg) | O'Higgins | - | Everton | 1:1 (1:0) | ||
| 1st(1st leg): 13/07/2019 22:30 | 2nd (2nd leg): 20/07/2019 22:30 | Winner: Everton | ||||
| 1st(1st leg) | Audax Italiano | - | Unión San Felipe | 0:0 (0:0) | ||
| 2nd (2nd leg) | Unión San Felipe | - | Audax Italiano | 0:1 (0:1) | ||
| 1st(1st leg): 14/07/2019 01:00 | 2nd (2nd leg): 20/07/2019 17:30 | Winner: Audax Italiano | ||||
| 1st(1st leg) | Deportes Iquique | - | Cobresal | 1:1 (0:1) | ||
| 2nd (2nd leg) | Cobresal | - | Deportes Iquique | 3:1 (2:1) | ||
| 1st(1st leg): 14/07/2019 17:00 | 2nd (2nd leg): 20/07/2019 20:00 | Winner: Cobresal | ||||
| 1st(1st leg) | Deportes Temuco | - | Universidad de Chile | 0:1 (0:1) | ||
| 2nd (2nd leg) | Universidad de Chile | - | Deportes Temuco | 2:0 (1:0) | ||
| 1st(1st leg): 14/07/2019 20:00 | 2nd (2nd leg): 20/07/2019 20:00 | Winner: Universidad de Chile | ||||
| 1st(1st leg) | Unión La Calera | - | Ñublense | 1:1 (0:0) | ||
| 2nd (2nd leg) | Ñublense | - | Unión La Calera | 4:5 (0:1, 1:1) pso | ||
| 1st(1st leg): 14/07/2019 22:30 | 2nd (2nd leg): 21/07/2019 20:00 | Winner: Unión La Calera | ||||
| 1st(1st leg) | Colo-Colo | - | Barnechea | 3:0 (1:0) | ||
| 2nd (2nd leg) | Barnechea | - | Colo-Colo | 0:3 (0:1) | ||
| 1st(1st leg): 15/07/2019 01:00 | 2nd (2nd leg): 21/07/2019 17:00 | Winner: Colo-Colo | ||||
| 1st(1st leg) | Santiago Morning | - | Universidad Católica | 0:2 (0:0) | ||
| 2nd (2nd leg) | Universidad Católica | - | Santiago Morning | 3:1 (1:1) | ||
| 1st(1st leg): 16/07/2019 21:00 | 2nd (2nd leg): 08/08/2019 01:00 | Winner: Universidad Católica | ||||
