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| 1st(1st leg) | San Luis | - | Audax Italiano | 2:4 (2:1) | ||
| 2nd (2nd leg) | Audax Italiano | - | San Luis | 4:3 (1:1, 1:3) pso | ||
| 1st(1st leg): 19/10/2016 00:00 | 2nd (2nd leg): 26/10/2016 00:00 | Winner: Audax Italiano | ||||
| 1st(1st leg) | Universidad Católica | - | Universidad de Chile | 2:0 (1:0) | ||
| 2nd (2nd leg) | Universidad de Chile | - | Universidad Católica | 3:3 (1:0) | ||
| 1st(1st leg): 20/10/2016 00:30 | 2nd (2nd leg): 25/10/2016 00:30 | Winner: Universidad Católica | ||||
| 1st(1st leg) | Cobreloa | - | Colo-Colo | 1:2 | ||
| 2nd (2nd leg) | Colo-Colo | - | Cobreloa | 3:1 (2:1) | ||
| 1st(1st leg): 21/10/2016 00:00 | 2nd (2nd leg): 26/10/2016 23:30 | Winner: Colo-Colo | ||||
| 1st(1st leg) | Unión Española | - | Everton | 1:2 (1:1) | ||
| 2nd (2nd leg) | Everton | - | Unión Española | 0:0 (0:0) | ||
| 1st(1st leg): 10/11/2016 23:30 | 2nd (2nd leg): 14/11/2016 23:30 | Winner: Everton | ||||
