England's chances of producing three semifinalists in the Champions League for the third successive season were dented by a tough-looking last 16 draw.

Defending champion Manchester United was paired with Italian champion and Serie A leader Inter Milan while Premier League leader Liverpool takes on nine-time champion Real Madrid after the draw was made at UEFA headquarters in Switzerland yesterday.

Last year's runner-up Chelsea was drawn with Juventus, managed by former Blues boss Claudio Ranieri, while Arsenal, finalists in 2006, plays 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.

Mourinho famously celebrated his Porto team's shock progress past United at the same stage in 2004 by running up and down the Old Trafford touchline to the ire of the home fans.

"Obviously Jose has put us out of the competition before," said United's communications director Phil Townsend in reference to Mourinho's success. "But equally we put Inter out in 1999 when we went on to win the tournament so maybe that's a good omen for us."

Real Madrid's meeting with Liverpool will mark only the second time that the Spanish champion has 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.

"It's mammoth, it really couldn't be a much bigger tie and I think our fans will be absolutely delighted that we've picked them up at this stage of the competition," said Liverpool secretary Bryce Morrison.

Liverpool boast by far the better form as Premier League leader while Real languishes sixth in the Spanish Primera Liga, a daunting 12 points behind leader 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," said Real Madrid director Jose Luis Lopez Serrano. "I'm sure there will be two very interesting games in Madrid and Liverpool."

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

"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.

Barcelona, the only non-English side to reach the semifinals last season, plays Olympique Lyon, which is in the knockout phase for the sixth successive season.

Villarreal, which reached the semifinals in its first appearance in 2006, drew Panathinaikos while the other pairings were Atletico Madrid vs Porto and Sporting vs Bayern Munich.

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

(Agencies via Shanghai Daily December 22, 2008)