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| 1st(1st leg) | Cobreloa | - | Universidad de Chile | 3:0 (1:0) | ||
| 2nd (2nd leg) | Universidad de Chile | - | Cobreloa | 3:2 (2:1) | ||
| 1st(1st leg): 15/11/2008 19:00 | 2nd (2nd leg): 23/11/2008 22:00 | Winner: Cobreloa | ||||
| 1st(1st leg) | Huachipato | - | Colo-Colo | 1:1 (1:1) | ||
| 2nd (2nd leg) | Colo-Colo | - | Huachipato | 4:2 (1:1) | ||
| 1st(1st leg): 15/11/2008 21:15 | 2nd (2nd leg): 22/11/2008 22:00 | Winner: Colo-Colo | ||||
| 1st(1st leg) | O'Higgins | - | Palestino | 2:2 (2:2) | ||
| 2nd (2nd leg) | Palestino | - | O'Higgins | 2:1 (1:0) | ||
| 1st(1st leg): 15/11/2008 23:30 | 2nd (2nd leg): 22/11/2008 19:30 | Winner: Palestino | ||||
| 1st(1st leg) | Universidad Católica | - | Rangers | 3:3 (1:1) | ||
| 2nd (2nd leg) | Rangers | - | Universidad Católica | 1:1 (0:0) | ||
| 1st(1st leg): 16/11/2008 19:00 | 2nd (2nd leg): 23/11/2008 19:30 | Winner: Rangers | ||||
