LONDON, Dec 19: England’s chances of producing three semi-finalists in the Champions League for the third successive season were dented on Friday by a tough-looking last-16 draw.

Holders Manchester United were paired with Italian champions and Serie A leaders Inter Milan while Premier League leaders Liverpool take on nine-time champions Real Madrid after the draw was made at UEFA headquarters in Nyon, Switzerland.

Last year’s runners-up Chelsea were paired with Juventus, managed by former Blues boss Claudio Ranieri, while Arsenal, finalists in 2006, play AS Roma in a third Anglo-Italian clash.

The Manchester United tie will see another former Chelsea boss, Jose Mourinho, returning to face Premiership opposition in his new role in charge of Inter.

Real Madrid’s meeting with Liverpool will mark only the second time that the Spanish nine-time European champions have met the English five-time winners in the competition.

Their only previous encounter came in the final of the 1981 European Cup with Liverpool winning 1-0.

Liverpool boast by far the better form as Premier League leaders while Real languish sixth in the Primera Liga, a daunting 12 points behind leaders Barcelona.

“The problem at our club is that we have had a lot of injured players but there is plenty of time for them to recover before we play Liverpool in February,” stated Real Madrid director Jose Luis Lopez Serrano.

Chelsea secretary David Barnard played down talk of Ranieri having the chance to take revenge against his former employers.

“I don’t think ‘revenge’ will be the right word for Claudio’s return because he was given a great reception by the fans when he left the club and I’m sure he’ll get one when he comes back,” Barnard said.

“He’ll know a lot of our players of course and the fact Juve got to the knockout stage shows that they’re a quality team.”

Barcelona, the only non-English side to reach the semi-finals last season, play Olympique Lyon, who are in the knockout phase for the sixth successive season.

Villarreal, who reached the semi-finals in their first appearance in 2006, drew Panathinaikos while the other pairings were Atletico Madrid v Porto and Sporting v Bayern Munich.

The ties take place on Feb 24-25 and March 10-11 with the final on May 27 in Rome.

Draw (last-16 stage):

Match 1: Chelsea (England) v Juventus (Italy)

Match 2: Villarreal (Spain) v Panathinaikos (Greece)

Match 3: Sporting Lisbon (Portugal) v Bayern Munich (Germany)

Match 4: Atletico Madrid (Spain) v FC Porto (Portugal)

Match 5: Lyon (France) v Barcelona (Spain)

Match 6: Real Madrid (Spain) v Liverpool (England)

Match 7: Arsenal (England) v Roma (Italy)

Match 8: Inter Milan (Italy) v Manchester United (England).—Agencies