Cruzeiro 1 – Univ de Chile 0 (Agg. 3-1) (Copa Libertadores last 16 second-leg, May 14, 2009) Kleber scored the only goal of the match and the home side are now unbeaten at the Mineirao Stadium in 24 successive matches.
Libertad 0 – Estudiantes 0 (Agg. 0-3) (Copa Libertadores last 16 second-leg, May 14, 2009) The Argentinean side defended their first-leg lead comfortably and are set to play the winner of the Defensor-Boca tie.
Defensor Sporting 2 – Boca Juniors 2 (Copa Libertadores last 16 first-leg, May 14, 2009) Boca are in pole position in the tie thanks to two away goals. Martin Palermo volleyed home the opener in the second minute. The home side hit back through Pablo Gaglianone only for Boca to take the lead again thanks to Rodrigo Palacio. Rodrigo Mora levelled things up late on.