The draw has set out an intriguing collection of ties, headlined by a few Brazil-Argentina clashes that are sure to provide plenty of drama.
Defending champion Flamengo will face Racing while Argentine giants Boca Juniors square off with Internacional. The third Argentina-Brazil clash will see 2018 champions River Plate battle Athletico Paranaense.
For the first time in Libertadores history, three Ecuadorian sides have qualified for the Round of 16. Liga de Quito face Group G winners Santos while Delfín take on Palmeiras, the side with the best group stage campaign. 2019 CONMEBOL Sudamericana champions Independiente del Valle battle Group F winners Nacional.
A pair of Paraguayan sides feature in the final two ties, with Libertad set to face surprise Group C winners Jorge Wilstermann while Guaraní, who started their Libertadores journey in the first phase, take on Group E winners Grêmio.
The draw also sets the bracket for the remainder of the competition, and while looking ahead in the Libertadores is always a fool's errand, a few tasty possibilities have been served up for later rounds.
The Round of 16 will start with first legs held the week of November 24th with the second legs to come during the following week. The Quarterfinals are set for mid-December while the semifinals and Final will take place in January with the date of the Final yet to be confirmed.