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| 1st(1st leg) | Boca Juniors | - | LDU Quito | 4:0 (2:0) | ||
| 2nd (2nd leg) | LDU Quito | - | Boca Juniors | 1:1 (0:1) | ||
| 1st(1st leg): 23/09/2008 23:30 | 2nd (2nd leg): 01/10/2008 23:30 | Winner: Boca Juniors | ||||
| 1st(1st leg) | Estudiantes | - | Arsenal de Sarandí | 2:1 (1:0) | ||
| 2nd (2nd leg) | Arsenal de Sarandí | - | Estudiantes | 0:0 (0:0) | ||
| 1st(1st leg): 24/09/2008 01:45 | 2nd (2nd leg): 03/10/2008 01:45 | Winner: Estudiantes | ||||
| 1st(1st leg) | Club San Luis | - | Argentinos Juniors | 2:1 (2:0) | ||
| 2nd (2nd leg) | Argentinos Juniors | - | Club San Luis | 2:0 (0:0) | ||
| 1st(1st leg): 24/09/2008 23:45 | 2nd (2nd leg): 02/10/2008 02:00 | Winner: Argentinos Juniors | ||||
| 1st(1st leg) | América de Cali | - | Botafogo - RJ | 1:0 (0:0) | ||
| 2nd (2nd leg) | Botafogo - RJ | - | América de Cali | 3:1 (1:0) | ||
| 1st(1st leg): 25/09/2008 02:00 | 2nd (2nd leg): 02/10/2008 02:00 | Winner: Botafogo - RJ | ||||
| 1st(1st leg) | Deportivo Guadalajara | - | Athletico Paranaense | 2:2 (1:1) | ||
| 2nd (2nd leg) | Athletico Paranaense | - | Deportivo Guadalajara | 3:4 (0:1) | ||
| 1st(1st leg): 25/09/2008 02:00 | 2nd (2nd leg): 01/10/2008 01:45 | Winner: Deportivo Guadalajara | ||||
| 1st(1st leg) | Sport Áncash | - | Palmeiras | 0:0 (0:0) | ||
| 2nd (2nd leg) | Palmeiras | - | Sport Áncash | 1:0 (0:0) | ||
| 1st(1st leg): 25/09/2008 02:00 | 2nd (2nd leg): 02/10/2008 02:00 | Winner: Palmeiras | ||||
| 1st(1st leg) | Defensor Sporting | - | River Plate | 1:2 (0:1) | ||
| 2nd (2nd leg) | River Plate | - | Defensor Sporting | 2:1 (1:0) | ||
| 1st(1st leg): 26/09/2008 00:00 | 2nd (2nd leg): 02/10/2008 23:15 | Winner: River Plate | ||||
| 1st(1st leg) | Universidad Católica | - | Internacional | 1:1 (1:0) | ||
| 2nd (2nd leg) | Internacional | - | Universidad Católica | 0:0 (0:0) | ||
| 1st(1st leg): 26/09/2008 02:15 | 2nd (2nd leg): 01/10/2008 21:00 | Winner: Internacional | ||||
