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| 1st(1st leg) | Unión Española | - | O'Higgins | 4:0 (2:0) | ||
| 2nd (2nd leg) | O'Higgins | - | Unión Española | 1:2 (0:1) | ||
| 1st(1st leg): 15/09/2016 22:30 | 2nd (2nd leg): 21/09/2016 22:30 | Winner: Unión Española | ||||
| 1st(1st leg) | Cobreloa | - | La Serena | 3:0 (2:0) | ||
| 2nd (2nd leg) | La Serena | - | Cobreloa | 0:0 (0:0) | ||
| 1st(1st leg): 16/09/2016 00:00 | 2nd (2nd leg): 28/09/2016 23:00 | Winner: Cobreloa | ||||
| 1st(1st leg) | Audax Italiano | - | Copiapó | 3:1 (1:0) | ||
| 2nd (2nd leg) | Copiapó | - | Audax Italiano | 2:2 (0:1) | ||
| 1st(1st leg): 16/09/2016 00:30 | 2nd (2nd leg): 28/09/2016 20:00 | Winner: Audax Italiano | ||||
| 1st(1st leg) | Huachipato | - | Colo-Colo | 2:1 (2:0) | ||
| 2nd (2nd leg) | Colo-Colo | - | Huachipato | 3:1 (1:0) | ||
| 1st(1st leg): 16/09/2016 19:00 | 2nd (2nd leg): 28/09/2016 00:00 | Winner: Colo-Colo | ||||
| 1st(1st leg) | Deportes Iquique | - | Universidad de Chile | 1:1 (0:1) | ||
| 2nd (2nd leg) | Universidad de Chile | - | Deportes Iquique | 7:6 (0:0, 2:2) pso | ||
| 1st(1st leg): 21/09/2016 20:00 | 2nd (2nd leg): 29/09/2016 00:00 | Winner: Universidad de Chile | ||||
| 1st(1st leg) | Universidad de Concepción | - | San Luis | 0:1 (0:1) | ||
| 2nd (2nd leg) | San Luis | - | Universidad de Concepción | 1:0 (0:0) | ||
| 1st(1st leg): 21/09/2016 23:30 | 2nd (2nd leg): 08/10/2016 23:00 | Winner: San Luis | ||||
| 1st(1st leg) | Universidad Católica | - | Deportes Temuco | 2:1 (1:0) | ||
| 2nd (2nd leg) | Deportes Temuco | - | Universidad Católica | 1:2 (0:0) | ||
| 1st(1st leg): 22/09/2016 01:00 | 2nd (2nd leg): 28/09/2016 21:30 | Winner: Universidad Católica | ||||
| 1st(1st leg) | Palestino | - | Everton | 0:1 (0:1) | ||
| 2nd (2nd leg) | Everton | - | Palestino | 1:1 (0:1) | ||
| 1st(1st leg): 07/10/2016 20:00 | 2nd (2nd leg): 03/11/2016 23:30 | Winner: Everton | ||||
