| Group 8 | 27/02/2009 | Club San Luis | - | Libertad | 0:1 | ||||
| Group 8 | 05/03/2009 | Libertad | - | San Lorenzo | 2:0 | ||||
| Group 8 | 18/03/2009 | San Lorenzo | - | Libertad | 0:1 | ||||
| Group 8 | 08/04/2009 | Universitario de Deportes | - | Libertad | 2:1 | ||||
| Group 8 | 29/04/2009 | Libertad | - | Club San Luis | 0:2 | ||||
| Round of 16 | 07/05/2009 | Estudiantes | - | Libertad | 3:0 | ||||
| Round of 16 | 15/05/2009 | Libertad | - | Estudiantes | 0:0 |
Uruguay