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| 1st(1st leg) | Cobreloa | - | Colo-Colo | 3:3 (2:2) | ||
| 2nd (2nd leg) | Colo-Colo | - | Cobreloa | 2:2 (1:1) | ||
| 1st(1st leg): 29/11/2008 19:00 | 2nd (2nd leg): 06/12/2008 23:15 | Winner: Colo-Colo | ||||
| 1st(1st leg) | Rangers | - | Palestino | 2:2 (2:0) | ||
| 2nd (2nd leg) | Palestino | - | Rangers | 0:0 (0:0) | ||
| 1st(1st leg): 30/11/2008 15:00 | 2nd (2nd leg): 06/12/2008 19:30 | Winner: Palestino | ||||
