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| 1st(1st leg) | Caracas FC | - | Grêmio Porto Alegre | 1:1 (1:0) | ||
| 2nd (2nd leg) | Grêmio Porto Alegre | - | Caracas FC | 0:0 (0:0) | ||
| 1st(1st leg): 28/05/2009 01:50 | 2nd (2nd leg): 18/06/2009 01:50 | Winner: Grêmio Porto Alegre | ||||
| 1st(1st leg) | Cruzeiro | - | São Paulo FC | 2:1 (1:0) | ||
| 2nd (2nd leg) | São Paulo FC | - | Cruzeiro | 0:2 (0:0) | ||
| 1st(1st leg): 28/05/2009 01:50 | 2nd (2nd leg): 19/06/2009 02:00 | Winner: Cruzeiro | ||||
| 1st(1st leg) | Defensor Sporting | - | Estudiantes | 0:1 (0:1) | ||
| 2nd (2nd leg) | Estudiantes | - | Defensor Sporting | 1:0 (1:0) | ||
| 1st(1st leg): 28/05/2009 23:45 | 2nd (2nd leg): 18/06/2009 23:30 | Winner: Estudiantes | ||||
| 1st(1st leg) | Palmeiras | - | Nacional | 1:1 (0:0) | ||
| 2nd (2nd leg) | Nacional | - | Palmeiras | 0:0 (0:0) | ||
| 1st(1st leg): 29/05/2009 02:00 | 2nd (2nd leg): 17/06/2009 23:20 | Winner: Nacional | ||||
