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| 1st(1st leg) | Chiapas FC | - | Nacional | dnp | ||
| 2nd (2nd leg) | Nacional | - | Chiapas FC | dnp | ||
| 1st(1st leg): | 2nd (2nd leg): | Winner: Chiapas FC | ||||
| 1st(1st leg) | Deportivo Guadalajara | - | São Paulo FC | dnp | ||
| 2nd (2nd leg) | São Paulo FC | - | Deportivo Guadalajara | dnp | ||
| 1st(1st leg): | 2nd (2nd leg): | Winner: Deportivo Guadalajara | ||||
| 1st(1st leg) | Palmeiras | - | Sport Recife - PE | 1:0 (0:0) | ||
| 2nd (2nd leg) | Sport Recife - PE | - | Palmeiras | 1:3 (0:0, 1:0, 1:0) pso | ||
| 1st(1st leg): 06/05/2009 01:15 | 2nd (2nd leg): 13/05/2009 00:15 | Winner: Palmeiras | ||||
| 1st(1st leg) | Universidad San Martín | - | Grêmio Porto Alegre | 1:3 (1:1) | ||
| 2nd (2nd leg) | Grêmio Porto Alegre | - | Universidad San Martín | 2:0 (1:0) | ||
| 1st(1st leg): 07/05/2009 01:50 | 2nd (2nd leg): 14/05/2009 01:50 | Winner: Grêmio Porto Alegre | ||||
| 1st(1st leg) | Deportivo Cuenca | - | Caracas FC | 2:1 (0:1) | ||
| 2nd (2nd leg) | Caracas FC | - | Deportivo Cuenca | 4:0 (2:0) | ||
| 1st(1st leg): 07/05/2009 21:20 | 2nd (2nd leg): 13/05/2009 01:15 | Winner: Caracas FC | ||||
| 1st(1st leg) | Estudiantes | - | Libertad | 3:0 (1:0) | ||
| 2nd (2nd leg) | Libertad | - | Estudiantes | 0:0 (0:0) | ||
| 1st(1st leg): 07/05/2009 23:40 | 2nd (2nd leg): 15/05/2009 02:00 | Winner: Estudiantes | ||||
| 1st(1st leg) | Universidad de Chile | - | Cruzeiro | 1:2 (0:1) | ||
| 2nd (2nd leg) | Cruzeiro | - | Universidad de Chile | 1:0 (0:0) | ||
| 1st(1st leg): 08/05/2009 02:00 | 2nd (2nd leg): 14/05/2009 23:30 | Winner: Cruzeiro | ||||
| 1st(1st leg) | Defensor Sporting | - | Boca Juniors | 2:2 (1:1) | ||
| 2nd (2nd leg) | Boca Juniors | - | Defensor Sporting | 0:1 (0:1) | ||
| 1st(1st leg): 14/05/2009 23:30 | 2nd (2nd leg): 21/05/2009 23:55 | Winner: Defensor Sporting | ||||
