Liverpool will face holders Real Madrid in the last 16 of the Champions League in a repeat of the 2022 final.
Real Madrid lifted the Champions League trophy for a 14th time back in May after a 1-0 win over Liverpool in Paris.
Liverpool and Real Madrid, who have 20 European Cups between them, will meet again in the Champions League, this time in the last-16 stage.
Premier League champions Manchester City, bidding to win the competition for the first time, were drawn to face RB Leipzig at Monday’s draw in Nyon, Switzerland.
Chelsea will face Borussia Dortmund while Tottenham face AC Milan for a place in the quarter-finals.
Elsewhere, French champions Paris Saint-Germain face a mouth-watering clash with German champions Bayern Munich.
Champions League last 16 draw
RB Leipzig v Manchester City
Club Bruges v Benfica
Liverpool v Real Madrid
AC Milan v Tottenham
Eintracht Frankfurt v Napoli
Borussia Dortmund v Chelsea
Inter Milan v Porto
Paris Saint-Germain v Bayern Munich
Teams who won their Champions League group were drawn against teams who finished second, while teams from the same country cannot play each other at this stage of the competition.
The last-16 first legs will take place on 14-15 and 21-22 February, with the second legs on 7-8 and 14-15 March.
The 2022-23 Champions League final will take place on June 10 at the Ataturk Olympic Stadium in Istanbul.
Liverpool ran the risk of drawing one of Europe’s best teams after only finishing second in Group A behind Serie A leaders Napoli.
Jurgen Klopp’s side impressed during the group stage – winning five of their six matches – but have endured an underwhelming start to the Premier League campaign to sit eighth after 13 games.
Liverpool will face a Real Madrid side who beat them in both the 2018 and 2022 Champions League finals, although the Reds did get their hands on the trophy in-between those two defeats as they beat Tottenham in 2019.
Manchester City have lost just one of their 18 games this season and will be confident of moving into the quarter-finals at the expense of Leipzig, who are just sixth in the Bundesliga.
Having topped Group E, Chelsea will feel hard done by after drawing German club Dortmund, who took points off Man City in the group stage and are only three points behind Bundesliga leaders Bayern Munich.
Tottenham have blown hot and cold this season but turned up when it mattered most to progress in Europe and will now turn their attentions to AC Milan, who were beaten twice by Chelsea in the group stage.
Away from the Premier League clubs, the stand-out fixture sees six-time winners Bayern Munich meet Paris Saint-Germain in a repeat of the 2020 final.
Bayern dominated Group C – scoring 18 goals and conceding just two in six games – but face a PSG side boasting the likes of Lionel Messi, Kylian Mbappe and Neymar.
Elsewhere, three-time European champions Inter Milan face two-time winners Porto, current Europa League champions Frankfurt meet Napoli and Club Bruges take on Benfica.
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