América de Cali 2-3 Botafogo/RJ *
| 02.10.2008 | Botafogo/RJ | 3-1 | América de Cali | |
| 25.09.2008 | América de Cali | 1-0 | Botafogo/RJ | |
*Estudiantes La Plata 2-1 Arsenal Sarandi
| 03.10.2008 | Arsenal Sarandi | 0-0 | Estudiantes La Plata | |
| 24.09.2008 | Estudiantes La Plata | 2-1 | Arsenal Sarandi | |
*Guadalajara Chivas 6-5 Atlético/PR
| 01.10.2008 | Atlético/PR | 3-4 | Guadalajara Chivas | |
| 25.09.2008 | Guadalajara Chivas | 2-2 | Atlético/PR | |
*Boca Juniors 5-1 LDU Quito
| 02.10.2008 | LDU Quito | 1-1 | Boca Juniors | |
| 24.09.2008 | Boca Juniors | 4-0 | LDU Quito | |
Defensor Sporting 2-4 River Plate *
| 03.10.2008 | River Plate | 2-1 | Defensor Sporting | |
| 26.09.2008 | Defensor Sporting | 1-2 | River Plate | |
San Luis FC 2-3 Argentinos Juniors *
| 02.10.2008 | Argentinos Juniors | 2-0 | San Luis FC | |
| 25.09.2008 | San Luis FC | 2-1 | Argentinos Juniors | |
Sport Ancash 0-1 Palmeiras/SP *
| 02.10.2008 | Palmeiras/SP | 1-0 | Sport Ancash | |
| 25.09.2008 | Sport Ancash | 0-0 | Palmeiras/SP | |
Universidad Católica 1-1 Internacional/RS *
| 01.10.2008 | Internacional/RS | 0-0 | Universidad Católica | |
| 26.09.2008 | Universidad Católica | 1-1 | Internacional/RS | |