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| 1st(1st leg) | Unión Española | - | La Serena | 1:1 (0:0) | ||
| 2nd (2nd leg) | La Serena | - | Unión Española | 2:1 (0:0) | ||
| 1st(1st leg): 21/11/2009 21:30 | 2nd (2nd leg): 24/11/2009 22:30 | Winner: La Serena | ||||
| 1st(1st leg) | Everton | - | Universidad Católica | 0:2 (0:0) | ||
| 2nd (2nd leg) | Universidad Católica | - | Everton | 0:0 (0:0) | ||
| 1st(1st leg): 22/11/2009 00:00 | 2nd (2nd leg): 25/11/2009 01:00 | Winner: Universidad Católica | ||||
| 1st(1st leg) | Universidad de Concepción | - | Colo-Colo | 1:2 (1:0) | ||
| 2nd (2nd leg) | Colo-Colo | - | Universidad de Concepción | 4:3 (3:2) | ||
| 1st(1st leg): 22/11/2009 20:00 | 2nd (2nd leg): 26/11/2009 00:15 | Winner: Colo-Colo | ||||
| 1st(1st leg) | Santiago Morning | - | Audax Italiano | 4:2 (2:0) | ||
| 2nd (2nd leg) | Audax Italiano | - | Santiago Morning | 2:1 (0:0) | ||
| 1st(1st leg): 22/11/2009 22:30 | 2nd (2nd leg): 25/11/2009 22:00 | Winner: Santiago Morning | ||||
