Defending champions Corinthians will face six-time winners Boca Juniors in the most eye-catching round of 16 contest in the Copa Libertadores.
The draw, made following the final round of group matches in this year's competition, also saw Brazil's Atletico Mineiro paired with compatriots Sao Paulo.
Santa Fe were paired with Gremio, Olimpia face Tigre, Velez Sarsfield come up against Newell's Old Boys, Garcilaso take on Nacional, Fluminense tackle Emelec and Palmeiras meet Tijuana.
Brazilian sides Gremio, Fluminense and Palmeiras completed the line-up, following the final round of group matches.
Fluminense and Gremio grabbed the top two positions in Group Eight after an exciting climax. The Brazilian side only needed a draw against Caracas but they beat the Venezuela side 1-0 thanks to a Rafael Sobis goal early in the second half.
Huachipato drew 1-1 with Gremio in Chile. Both teams finished levelled on eight points - but the Brazilians qualified thanks to a better goal difference.
Ze Roberto opened the scoring in the first half but two minutes before the end Huachipato set up an exciting climax with an equaliser from Miguel Aceval.
Palmeiras finished top of Group Two, despite losing 1-0 to an Irven Avila goal for Sporting Cristal in Peru.
Argentina's Tigre claimed the second position after a 5-3 victory in Paraguay over Libertad.
Libertad needed only a draw to qualify, but found themselves behind to a goal from Ruben Botta in the 10th minute. Miguel Samudio equalised, but Matias Perez Garcia put the Argentinians ahead and Gaston Diaz's penalty made it 3-1, before Jose Nunez reduced the arrears just before the break.
Perez Garcia and Botta both scored their second goals to put Tigre out of sight - but a goal by Pablo Velazquez for Libertad in injury-time denied them top spot on goal difference.