Liverpool have a chance to get early revenge on Real Madrid following last season's Champions League final heartbreak after being drawn against them in the Round of 16.
In arguably the tie of the draw, Jurgen Klopp's side must come out on top against Carlo Ancelotti's men over two legs after they beat them 1-0 in Paris just six months ago.
Pep Guardiola's Manchester City face an easier test in RB Leipzig. Elsewhere, Graham Potter Chelsea's play Dortmund, while Antonio Conte and Tottenham have been drawn against AC Milan.
The last-16 first legs are scheduled to take place on 14-15 and 21-22 February, with the second legs taking place a month later on 7-8 and 14-15 March.
The Champions League last-16 draw took place in Nyon, Switzerland this Monday, where seeded teams - those who won their respective groups - were drawn against those who finished second.
Teams from the same country are not able to face off against each other at this stage in the tournament.
Chelsea, Man City and Spurs all won their groups and were handed, on paper at least, favourable ties, while Liverpool, who finished second in theirs, are faced with a much tougher challenge in last season's champions.
Liverpool finished second to Napoli in their group on goal difference after both sides accrued 15 points from a possible 18 available.
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Spurs won their group in dramatic fashion, beating second-place Frankfurt to the top spot by a point. Ligue 1 side Marseille and Portuguese giants Sporting Lisbon were both sent home.
Chelsea won Group E at the expense of Milan, with Salzburg and Dinamo Zagreb both being eliminated, while Man City qualified at a canter with a five-point advantage over second-place Dortmund.
Full Champions League last-16 draw:
RB Leipzig vs Manchester City
Club Brugge vs Benfica
Liverpool vs Real Madrid
AC Milan vs Tottenham
Eintracht Frankfurt vs Napoli
Borussia Dortmund vs Chelsea
Inter Milan vs Porto
Paris Saint-Germain vs Bayern Munich
