Estudiantes 1 – Defensor Sporting 0 (Agg. 2-0) (Copa Libertadores, June 18, 2009) Estudiantes went in front in the 14th minute when midfielder Leandro Benitez applied the finishing touch following a nice move down the left.
Sao Paulo 0 – Cruzeiro 2 (Agg. 1-4) (Copa Libertadores, June 18, 2009) Sao Paulo had Eduardo Costa sent off just before the interval. Sao Paulo were made to pay in the 65th minute when Henrique beat keeper Denis from the edge of the box with a powerful strike. Cruzeiro killed the tie ten minutes from time when Andre Dias was sent off after handling inside the area and Kleber made no mistake from the spot.