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| 1st(1st leg) | Unión San Felipe | - | Universidad de Chile | 1:2 (1:0) | ||
| 2nd (2nd leg) | Universidad de Chile | - | Unión San Felipe | 1:1 (1:0) | ||
| 1st(1st leg): 25/05/2011 23:00 | 2nd (2nd leg): 28/05/2011 23:00 | Winner: Universidad de Chile | ||||
| 1st(1st leg) | O'Higgins | - | Palestino | 1:1 (1:0) | ||
| 2nd (2nd leg) | Palestino | - | O'Higgins | 0:3 (0:1) | ||
| 1st(1st leg): 26/05/2011 01:00 | 2nd (2nd leg): 28/05/2011 20:30 | Winner: O'Higgins | ||||
| 1st(1st leg) | Unión La Calera | - | Unión Española | 1:0 (0:0) | ||
| 2nd (2nd leg) | Unión Española | - | Unión La Calera | 0:0 (0:0) | ||
| 1st(1st leg): 26/05/2011 21:00 | 2nd (2nd leg): 29/05/2011 23:00 | Winner: Unión La Calera | ||||
| 1st(1st leg) | Colo-Colo | - | Universidad Católica | 2:4 (2:1) | ||
| 2nd (2nd leg) | Universidad Católica | - | Colo-Colo | 1:1 (0:0) | ||
| 1st(1st leg): 27/05/2011 01:00 | 2nd (2nd leg): 29/05/2011 21:00 | Winner: Universidad Católica | ||||
