Coritiba 2-0 Vitória
Vitória advances 5–3 on penalties
Libertad Asunción 1-1 Liga de Quito
Liga de Quito advances 4-1 on points
Unión Española 1-0 La Equidad Bogotá
Unión Española advances 4-1 on points
Flamengo 1-1 Fluminense
Fluminense advances on away goals
River Plate 2-1 Blooming Santa Cruz
River advances 6-0 on points
Emelec Guayacil 2-1 Zamora
Emelec Guayacil advances 6-0 on points
The 2008 Libertadores winners Liga de Quito advanced to the last 16 after a 1-1 draw in Asunción on Tuesday night. They did it the hard way though, coming from a Javier Gonzales goal down to snatch a draw thanks to a goal from Edison Méndez with 25 minutes to go. Despite defeating Vitória 2-0, Coritiba were eliminated after the tie went to a penalty shoot out. Marcelinho and Renathino got second half goals for Coritiba but they ultimately came up short from 12 yards. After a 2-2 draw in the first leg in Colombia, Unión Española triumphed 1-0 in the return leg to progress. The match winner, a 17th minute strike from Mauricio Aravena.
At the Maracaña, 9 man Flamengo were eliminated by bitter rivals Fluminense on away goals. Fluminense went ahead just before half time when Roni converted from the penalty spot. Flamengo, knowing they had to score twice to progress, threw everything bar the kitchen sink at Fluminense. They finally levelled on the hour after a shot from Denis Marques took a deflection and found the back of the net. Flamengo became frustrated as they chased a winner, with David and Gonzalo Fierro both seeing red in the last 10 minutes.
After the fun and games of the first leg, River Plate Montevideo and Blooming actually managed to complete their fixture in the Centenario. All the goals came in the last 10 minutes of the game, Jorge Córdoba putting River ahead. Blooming equalized almost immediately through Jose Luis Chavez but three minutes from time Bruno Montelongo grabbed the victory for River from close range. In Ecuador, Emelec came from a goal down to progress against Zamora. Giovanny Perez levelled the tie after 27 minutes and when the home side had Jose Lius Quinonez sent off 7 minutes later it was looking good for Zamora. Emelec though levelled through Franco Mendoza with 20 minutes to go and snatched the win in the last minute through Hernan Peirone. Zamora were then reduced to 9 players when Ruben Speroni and Ronald Castillo were both dismissed in injury time.