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| U | Cobreloa | - | Universidad de Chile | 3:0 (1:0) | ||
| R | Universidad de Chile | - | Cobreloa | 3:2 (2:1) | ||
| U: 15.11.2008 20:00 | R: 23.11.2008 23:00 | Winnaars: Cobreloa | ||||
| U | Huachipato | - | Colo-Colo | 1:1 (1:1) | ||
| R | Colo-Colo | - | Huachipato | 4:2 (1:1) | ||
| U: 15.11.2008 22:15 | R: 22.11.2008 23:00 | Winnaars: Colo-Colo | ||||
| U | O'Higgins | - | Palestino | 2:2 (2:2) | ||
| R | Palestino | - | O'Higgins | 2:1 (1:0) | ||
| U: 16.11.2008 00:30 | R: 22.11.2008 20:30 | Winnaars: Palestino | ||||
| U | Universidad Católica | - | Rangers | 3:3 (1:1) | ||
| R | Rangers | - | Universidad Católica | 1:1 (0:0) | ||
| U: 16.11.2008 20:00 | R: 23.11.2008 20:30 | Winnaars: Rangers | ||||
