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| H (Match allé) | Audax Italiano | - | Universidad de Chile | 1:4 (0:1) | ||
| R (match retour) | Universidad de Chile | - | Audax Italiano | 2:4 (1:2) | ||
| H (Match allé): 13.06.2009 21:30 | R (match retour): 21.06.2009 00:30 | vainqueur: Universidad de Chile | ||||
| H (Match allé) | O'Higgins | - | Unión Española | 1:1 (1:1) | ||
| R (match retour) | Unión Española | - | O'Higgins | 6:1 (4:0) | ||
| H (Match allé): 14.06.2009 00:00 | R (match retour): 21.06.2009 18:00 | vainqueur: Unión Española | ||||
| H (Match allé) | Municipal Iquique | - | Everton | 2:2 (1:1) | ||
| R (match retour) | Everton | - | Municipal Iquique | 2:1 (0:0) | ||
| H (Match allé): 14.06.2009 22:00 | R (match retour): 21.06.2009 22:00 | vainqueur: Everton | ||||
| H (Match allé) | Universidad Católica | - | Santiago Morning | 4:0 (3:0) | ||
| R (match retour) | Santiago Morning | - | Universidad Católica | 1:4 (0:2) | ||
| H (Match allé): 17.06.2009 02:00 | R (match retour): 22.06.2009 00:30 | vainqueur: Universidad Católica | ||||
