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| 1st(1st leg) | Everton | - | Universidad de Chile | 1:0 (0:0) | ||
| 2nd (2nd leg) | Universidad de Chile | - | Everton | 3:1 (2:0) | ||
| 1st(1st leg): 25/06/2009 01:00 | 2nd (2nd leg): 27/06/2009 21:00 | Winner: Universidad de Chile | ||||
| 1st(1st leg) | Universidad Católica | - | Unión Española | 0:0 (0:0) | ||
| 2nd (2nd leg) | Unión Española | - | Universidad Católica | 4:2 (0:0, 0:0, 0:0) pso | ||
| 1st(1st leg): 26/06/2009 01:00 | 2nd (2nd leg): 29/06/2009 17:00 | Winner: Unión Española | ||||
