| 1. Round | 28/08/2008 | Aragua FC | - | Deportivo Guadalajara | 1:2 | ||||
| 1. Round | 18/09/2008 | Deportivo Guadalajara | - | Aragua FC | 1:1 | ||||
| Round of 16 | 01/10/2008 | Athletico Paranaense | - | Deportivo Guadalajara | 3:4 | ||||
| Quarter-finals | 22/10/2008 | River Plate | - | Deportivo Guadalajara | 1:2 |  |
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| Quarter-finals | 07/11/2008 | Deportivo Guadalajara | - | River Plate | 2:2 | ||||
| Semi-finals | 13/11/2008 | Deportivo Guadalajara | - | Internacional | 0:2 | ||||
| Semi-finals | 20/11/2008 | Internacional | - | Deportivo Guadalajara | 4:0 |
Mexico