Cruzeiro 3 – Gremio 1 (Copa Libertadores semi-final first-leg June 24, 2009) Maxi Lopez missed a great chance for Gremio early on and the home side took full advantage. Wellington headed the opener and further goals from Wagner and Fabinho gave them one foot in the final. A fine free-kick from Souza left Gremio with plenty of hope for the second leg.
Once Caldas 2 – Atletico Junior 1 (Colombian Apertura play-off, June 24, 2009) A billiant dipping swerving shot from Nondier Romero gave Once Caldas the lead, Fano doubled the lead before Hernandez pulled one back.
Everton CD 1 – Univ. de Chile 0 (Chilean Apertura play-off, June 24, 2009)