Thirteen-time winners Real Madrid were drawn against English champions Manchester City while title-holders Liverpool must face Diego Simeone’s Atletico Madrid in the Champions League round of 16 following Monday’s draw.

Real Madrid ended up in pot two after finishing second in their group behind Paris St Germain and City were the unlucky team to be paired with them when their name was pulled out at Uefa headquarters.

City, who will be at home in the second leg, have yet to beat the Spanish side with two draws and two defeats in their previous four meetings.

However, their manager Pep Guardiola has a more encouraging record with nine wins, four draws and four defeats in 17 meetings as coach of Barcelona and then Bayern Munich.

“It’s a difficult one,” said Manchester City’s director of football Txiki Begiristain. “Real Madrid are the best. We want to be the best so we have to try and beat them.”

Liverpool and Atletico Madrid’s previous meetings have produced one win for each team and two draws with both teams scoring four goals.

Only Europe’s biggest five leagues — England, France, Germany, Italy and Spain — were represented in the draw and 11 of the 16 teams also reached the knockout stages last season.

Serie A champions Juventus will face French side Olympique Lyonnais and PSG will play Borussia Dortmund.

Barcelona were pitted against an unpredictable Napoli, the first time the two sides have ever met.

Napoli fired coach Carlo Ancelotti immediately after beating Genk to make sure of their place in the last 16 and replaced him with Gennaro Gattuso, who has never coached in the Champions League before.

Jose Mourinho’s Tottenham Hotspur, which reached the final last season, will play RB Leipzig while Chelsea were drawn against Bayern Munich.

Despite their erratic domestic form, Bayern were the only team to complete the group stage with a 100 per cent record. Serie A side Atalanta were drawn against Valencia.

United vs Brugge

Manchester United will continue their Europa League campaign against Belgian side Club Brugge after Monday’s draw for the last 32 of the competition.

Three-time European champions United, arguably the biggest name in the draw, qualified as group winners while Brugge drop in from the Champions League after finishing behind Paris St Germain and Real Madrid.

Ajax Amsterdam’s consolation for exiting the Champions League at the group phase is a two-legged tie with Spanish side Getafe, while Inter Milan face Bulgarians Ludogorets.