Group 4 | 25/02/2009 | Independiente Medellín | - | Defensor Sporting | 0:0 | ||||
Group 4 | 09/04/2009 | São Paulo FC | - | Defensor Sporting | 2:1 | ||||
Round of 16 | 21/05/2009 | Boca Juniors | - | Defensor Sporting | 0:1 | ||||
Quarter-finals | 18/06/2009 | Estudiantes | - | Defensor Sporting | 1:0 |