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| H | Boca Juniors | - | LDU Quito | 4:0 (2:0) | ||
| R | LDU Quito | - | Boca Juniors | 1:1 (0:1) | ||
| H: 24.09.2008 00:30 | R: 02.10.2008 00:30 | Sieger: Boca Juniors | ||||
| H | Estudiantes | - | Arsenal de Sarandí | 2:1 (1:0) | ||
| R | Arsenal de Sarandí | - | Estudiantes | 0:0 (0:0) | ||
| H: 24.09.2008 02:45 | R: 03.10.2008 02:45 | Sieger: Estudiantes | ||||
| H | Club San Luis | - | Argentinos Juniors | 2:1 (2:0) | ||
| R | Argentinos Juniors | - | Club San Luis | 2:0 (0:0) | ||
| H: 25.09.2008 00:45 | R: 02.10.2008 03:00 | Sieger: Argentinos Juniors | ||||
| H | América de Cali | - | Botafogo - RJ | 1:0 (0:0) | ||
| R | Botafogo - RJ | - | América de Cali | 3:1 (1:0) | ||
| H: 25.09.2008 03:00 | R: 02.10.2008 03:00 | Sieger: Botafogo - RJ | ||||
| H | Deportivo Guadalajara | - | Athletico Paranaense | 2:2 (1:1) | ||
| R | Athletico Paranaense | - | Deportivo Guadalajara | 3:4 (0:1) | ||
| H: 25.09.2008 03:00 | R: 01.10.2008 02:45 | Sieger: Deportivo Guadalajara | ||||
| H | Sport Áncash | - | Palmeiras | 0:0 (0:0) | ||
| R | Palmeiras | - | Sport Áncash | 1:0 (0:0) | ||
| H: 25.09.2008 03:00 | R: 02.10.2008 03:00 | Sieger: Palmeiras | ||||
| H | Defensor Sporting | - | River Plate | 1:2 (0:1) | ||
| R | River Plate | - | Defensor Sporting | 2:1 (1:0) | ||
| H: 26.09.2008 01:00 | R: 03.10.2008 00:15 | Sieger: River Plate | ||||
| H | Universidad Católica | - | Internacional | 1:1 (1:0) | ||
| R | Internacional | - | Universidad Católica | 0:0 (0:0) | ||
| H: 26.09.2008 03:15 | R: 01.10.2008 22:00 | Sieger: Internacional | ||||
