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| 1st(1st leg) | Audax Italiano | - | Universidad de Chile | 1:4 (0:1) | ||
| 2nd (2nd leg) | Universidad de Chile | - | Audax Italiano | 2:4 (1:2) | ||
| 1st(1st leg): 13/06/2009 20:30 | 2nd (2nd leg): 20/06/2009 23:30 | Winner: Universidad de Chile | ||||
| 1st(1st leg) | O'Higgins | - | Unión Española | 1:1 (1:1) | ||
| 2nd (2nd leg) | Unión Española | - | O'Higgins | 6:1 (4:0) | ||
| 1st(1st leg): 13/06/2009 23:00 | 2nd (2nd leg): 21/06/2009 17:00 | Winner: Unión Española | ||||
| 1st(1st leg) | Municipal Iquique | - | Everton | 2:2 (1:1) | ||
| 2nd (2nd leg) | Everton | - | Municipal Iquique | 2:1 (0:0) | ||
| 1st(1st leg): 14/06/2009 21:00 | 2nd (2nd leg): 21/06/2009 21:00 | Winner: Everton | ||||
| 1st(1st leg) | Universidad Católica | - | Santiago Morning | 4:0 (3:0) | ||
| 2nd (2nd leg) | Santiago Morning | - | Universidad Católica | 1:4 (0:2) | ||
| 1st(1st leg): 17/06/2009 01:00 | 2nd (2nd leg): 21/06/2009 23:30 | Winner: Universidad Católica | ||||
