Paraguayan side Libertad became the first team to qualify for the Copa Libertadores Round of 16 with a 1-0 Group 1 victory over Universidad San Martin 1-0 in Peru on Tuesday night.
A 24th-minute penalty by Sergio Aquino proved decisive for Gregorio Perez's side, a minute after the dismissal of San Martin defender Julio Moreyra. Libertad goalkeeper Tobias Vargas also saved a first-half penalty from Heber Arriola.
A left-footed strike by Luis Nunez put Once Caldas ahead 12 minutes from time only for Juan Carlos Medina to equalise with a long-range effort in stoppage time. Once Caldas captain Alexis Henriquez and San Luis defender Sergio Ponce were both sent off following a fight in the closing minutes. Another San Luis player, Guillermo Rangel, who also red-carded from the bench.
Libertad have collected ten points so far in Group 1 - four more than San Martin, while Once Caldas (three points) and San Luis (two points) have little hope of qualifying.
Uruguayan giants Nacional claimed their first win in Copa Libertadores Group 3 with a 1-0 win over Argentinos Juniors in Argentina. The result was extra sweet for Juan Ramon Carrasco's team, coming a week after they lost 1-0 at home to Argentinos.
Santiago Garcia netted the winner in the 33rd minute after a mistake by defender Santiago Gentiletti. Despite a first defeat in the group, Argentinos retain top spot in the pool with seven points - one more than Mexican giants America and three above Nacional.
"We had to give joy to our fans who came to Argentina to see us. We are happy because we clinched a great win tonight," Garcia told Fox Sports. "We played well in the whole match. We believe in ourselves."