Pep Guardiola will renew rivalries with Real Madrid after Manchester City were drawn to face Los Blancos in a blockbuster Champions League last-16 tie. (More Football News)
With City 14 points adrift of leaders Liverpool in the Premier League, success in Europe is likely to be Guardiola's main priority this season.
But their hopes of glory in the continent's premier club competition were not helped by a daunting clash with La Liga giants Madrid, who have triumphed in four of the past six editions.
Guardiola is no stranger to Madrid having spent four years in charge of their fierce Clasico rivals Barcelona, while he was Bayern Munich coach when they were defeated 5-0 over two legs in the 2013-14 Champions League semi-finals.
Madrid have previous against City in the competition, too, coming out on top in a last-four clash in the 2015-16 campaign.
We’ve been drawn against Real Madrid in the @ChampionsLeague Round of 16.December 16, 2019
Holders Liverpool face Atletico Madrid – runners-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 they became European champions for a sixth time.
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
Round of 16 drawDecember 16, 2019
The first legs will take place on 18, 19, 25 and 26 February, with the return fixtures set for 10, 11, 17 and 18 March.
Club dignitaries will return to Nyon on March 20 for the draw for the quarter-finals and semi-finals.
Jurgen Klopp's side finished top of Group E by a solitary point from Napoli, who have the unenvious task of facing LaLiga champions 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 their runners-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 favourites in their tie against Lyon, while fellow Serie A side Atalanta – who made the last 16 in their first endeavour into the Champions League – go up against Valencia for a place in the quarter-finals.