England's chances of producing three semifinalists in the Champions League for the third successive season were dented on Friday by a tough-looking last 16 draw. 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 Nyon, Switzerland. Last year's runner-up Chelsea was paired with Juventus, managed by former Blues boss Claudio Ranieri, while Arsenal, finalist 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. “Obviously Jose has put us out of the competition before,” said United's communications director Phil Townsend in reference to Mourinho's success at the same stage in 2004 with eventual European champion Porto. “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 nine-time European champion has met the English five-time winner in the competition. It 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 club secretary Bryce Morrison. Liverpool boasts by far the better form as Premier League leader while Real languishes sixth in the Primera Liga, a daunting 12 points behind leaders Barcelona. 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,” he said. Barcelona 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 Feb. 24-25 and March 10-11 with the final on May 27 in Rome. – ReutersMilan vs. Bremen in UEFA CupLONDON – Competition favorite AC Milan will face Werder Bremen, one of the Champions League dropouts, in the last 32 of the UEFA Cup following Friday's draw in Nyon, Switzerland. The Italians, seven-time European champion but who have never won the UEFA Cup, were sure to meet one of the Champions League third-place finishers after its 2-2 home draw with VfL Wolfsburg on Wednesday allowed the German side to top its qualifying group. Bremen finished behind Panathinaikos and Inter Milan in its Champions League group. Wolfsburg's reward is a game against Paris St. Germain, which sneaked through on goal difference thanks to its 4-0 win over Twente Enschede in their final group game this week. If Milan progresses it will meet either Olympiakos Piraeus or St. Etienne in the last 16 after the draw for that round was also carried out at UEFA headquarters. Champion Zenit St. Petersburg was drawn against VfB Stuttgart in the first knockout round. If Zenit wins it will play either Udinese or Polish outsider Lech Poznan. Four-time European champion Ajax Amsterdam will play Fiorentina. The last-32 ties will be played over two legs on Feb 18
