Pep Guardiola will renew rivalries with Real Madrid after Manchester City was drawn to face Los Blancos in a blockbuster Champions League last-16 tie.
With City 14 points adrift of leader Liverpool in the Premier League, success in Europe is likely to be Guardiola's main priority this season.
But its hopes of glory in the continent's premier club competition was not helped by a daunting clash with La Liga giant Madrid, who has triumphed in four of the past six editions.
Highlights: Champions League draw
Guardiola is no stranger to Madrid having spent four years in charge of its fierce Clasico rivals Barcelona, while he was Bayern Munich coach when it was defeated 5-0 over two legs in the 2013-14 Champions League semifinals.
Madrid has previous against City in the competition, too, coming out on top in a last-four clash in the 2015-16 campaign.
Holder Liverpool faces Atletico Madrid – runner-up in 2013-14 and 2015-16 – in a return to the Wanda Metropolitano, the scene of the Reds' 2-0 win over Tottenham in last season's final as it became European champion for a sixth time.
Jurgen Klopp's side finished top of Group E by a solitary point from Napoli, who has the unenvious task of facing La Liga champion Barcelona – aiming to get their hands on European football's most coveted prize for the first time since 2014-15.
In a draw brimming with sub-plots, Thomas Tuchel will return to Borussia Dortmund with his Paris Saint-Germain side, while Chelsea and Bayern Munich – the only team to win all six of their group-stage games – face off in what is a rematch of the 2011-2012 final.
Tottenham, aiming to beat its runner-up finish last term, go head-to-head with an RB Leipzig side playing in the knockout stages for the first time.
Juventus will start as favourite in its tie against Lyon, while fellow Serie A side Atalanta – which made the last 16 in its first endeavour into the Champions League – go up against Valencia for a place in the quarterfinals.
The first-leg matches will take place on February 18, 19, 25 and 26, with the return fixtures played on March 10, 11, 17 and 18.
The draw for the last 16 of the 2019-20 Champions League is:
Borussia Dortmund vs Paris Saint-Germain
Real Madrid vs Manchester City
Atalanta vs Valencia
Atletico Madrid vs Liverpool
Chelsea vs Bayern Munich
Lyon vs Juventus
Tottenham vs RB Leipzig
Napoli vs Barcelona
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