The four Premier League sides through to the last 16 face difficult task to progress to the Champions League quarter-finals after Monday morning's draw in Nyon paired the quartet with some tricky opponents.
Favourites Manchester City, through as group winners, were drawn against 13-time winners of the competition Real Madrid who finished second in their group behind Paris Saint-Germain.
Liverpool face Real's city rivals Atletico with Diego Simeone's side notoriously stubborn opponents to negotiate over two legs in European knockout competition.
Frank Lampard's Chelsea, who finished as runners-up to Valencia in Group H, were handed the daunting task of playing Bundesliga champions Bayern Munich. The Bavarians won all six of their group matches including a 7-2 thrashing of Tottenham in north London.
Tottenham themselves qualified in second behind Bayern and take on another German opponent, RB Leipzig, who made it through to the knockout stages for the first time in their history.
Borussia Dortmund v Paris Saint-Germain
Real Madrid v Manchester City
Atalanta v Valencia
Atletico Madrid v Liverpool
Chelsea v Bayern Munich
Lyon v Juventus
Tottenham v RB Leipzig
Napoli v Barcelona
*Team A are runners-up, Team B are group winners
Elsewhere Napoli drew Barcelona, Lyon were pitted against Juventus, Borussia Dortmund will play PSG and surprise packages Atalanta face La Liga outfit Valencia.
Real were City's opponents when they made it to the furthest stage they have managed in their competition, in the 2015/16 season. Manuel Pellegrini's side were beaten 1-0 over two legs as Real went on to win the competition under Zinedine Zidane.
This campaign City are favourites to win the competition under Pep Guardiola with rivals Liverpool looking nailed on to clinch the domestic league title after dropping just two points in their opening 17 Premier League matches.
Guardiola has lost out in the quarter-finals in each of his three seasons at the Etihad and last year saw City crash out due to a late VAR intervention that chalked off Raheem Sterling's would-be winner against Tottenham.
Real meanwhile have been hit-and-miss this season following the return of Zidane but boast unrivalled pedigree in Europe's most prestigious club competition having won three consecutive titles between 2016 and 2018.
Liverpool, who saw off Tottenham in last season's final in Madrid, are back in the Spanish capital to face Atletico in their bid for a place in the quarter-finals.
Jurgen Klopp's side overcame Spanish opposition in Barcelona last season in the semi-finals when they overturned a three-goal first-leg deficit to see off Barcelona 4-0 at Anfield.
Atletico though are reknowned for their defensive solidity and boast the meanest defence in La Liga this season, having leaked just 10 goals in their opening 17 matches.
The Mattress Makers boast significant pedigree in the competition having made the final in 2014 and 2016, on both ocassions succumbing to city rivals Real.
The two sides have faced each other four times in European competition with Atletico winning once, Liverpool winning once and two draws with the most recent fixture a Europa League semi-final in 2010 won by the English side.
Monday's draw has also served up a rematch of the 2012 Champions League final as Chelsea face Bayern Munich over two legs in a bid to make the quarter-finals.
Lampard was a player in Munich when Chelsea staged a dramatic late comeback thanks to Didier Drogba's header to see off the German giants on home soil via a penalty shootout.
This season's Chelsea are in the midst of a poor run of domestic form but were able to qualify in second place in Group H thanks to big wins at Ajax and over French side Lille.
Bayern meanwhile have endured a tough season in the Bundesliga with previous coach Niko Kovac paying the price with his job.
However in Europe they've not put a foot wrong and finished the group stages with six wins from six and 24 goals scored - the most managed by any side in the competition.
Seven of those came in the mauling of Tottenham with ex-Arsenal man Serge Gnabry netting four times while Robert Lewandowski has scored 10 across the six matches.
Tottenham, coached by two-time Champions League winner Jose Mourinho, were handed a somewhat kinder draw after being pitted against Bundesliga leaders RB Leipzig.
Spurs appear to be back on track under Mourinho after Mauricio Pochettino's regime came to a disappointing end with a disastrous start to the season. They qualified in second place behind Bayern Munich thanks to wins over Olympiacos and Red Star Belgrade.
Leipzig topped a relatively even Group G ahead of Lyon, Benfica and Zenit St Petersburg and boast a lethal marksman in Germany international Timo Werner.
Despite their lack of pedigree in the competition - this is just their second season on Europe's biggest stage - Julian Nagelsmann's side represent tricky opponents for Tottenham.
Away from English interest, Dortmund and PSG were paired up in an intriguing tie between two of Europe's most exciting attacking teams. The fixture sees PSG coach Thomas Tuchel return to his former club Dortmund, who finished as runners-up behind Barcelona in Group F.
PSG secured a stunning 3-0 win over Real Madrid in the group stages while Dortmund qualified ahead of Inter Milan thanks in part to a goalless draw againsr Barcelona and a home victory over the Italians.
Two of Diego Maradona's former clubs go head-to-head as Group F winners Barcelona take on Group E runners-up Napoli.
Barcelona are still smarting from their disastrous semi-final collapse against Liverpool last year but topped a difficult group ahead of Dortmund, Inter and Slavia Prague.
Napoli meanwhile are in dissaray following the dismissal of their manager Carlo Ancelotti and subsequent installment of Gennaro Gattuso as his replacement.
The Serie A side defeated the holders Liverpool at the Stadio San Paolo and drew with The Reds at Anfield to edge out Red Bull Salzburg for a place in the quarter-finals.
Elsewhere in Italy, eight-time Serie A champions Juventus and Cristiano Ronaldo face perhaps the easiest opponents of the round having been pitted against Ligue 1 side Lyon.
Juventus are out to secure their first Champions League success since 1996 and were in the final as recently as 2017, when they lost out to a Ronaldo-inspired Real Madrid.
Lyon edged through to the knockout stages thanks to wins over RB Leipzig and Benfica but have struggled domestically this campaign and recently made a managerial change - re-appointing Rudi Garcia as coach.
They have been hit by a serious injury to key player and former Manchester United winger Memphis Depay.
The final tie of the round sees Group H winners Valencia, who made the Europa League semi-finals last season, host Italian upstarts Atalanta - who qualified despite losing their opening three group-stage matches.
How does the draw work?
No team can play a club from either their Champions League group or the same national association, meaning there can be no all-Premier League ties in the last 16.
The group winners, or seeded teams, will play the second legs at home.
When will the last 16 ties take place?
The first legs, with the runners-up at home, will take place across two weeks in February with two matches per night. Half of the ties will get underway on Tuesday 18 and Wednesday 19, with the remaining eight first leg ties being played on Tuesday 25 and Wednesday 26.
The second legs, with the seeded group winners at home, will follow the same format and be played across four different nights. The dates for your diary are Tuesday 10 and Wednesday 11 March, followed by Tuesday 17 and Wednesday 18.
All matches will kick off at 8pm and the draw for the quarter-finals, semi-finals and final will take place on Friday 20 March following their conclusion.
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