England's chances of producing three semi-finalists in the Champions League for the third successive season were dented today by a tough-looking last 16 draw.
Holders Manchester United were paired with Italian champions and Serie A leaders Inter while Premier League leaders Liverpool take on nine-times champions Real Madrid after the draw made at UEFA headquarters in Nyon, Switzerland.
Last year's runners-up Chelsea were paired with Juventus, managed by former Chelsea boss Claudio Ranieri, while Arsenal, finalists in 2006, play AS Roma in a third Anglo-Italian clash.
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 February 24/25 and March 10/11 with the final on May 27 in Rome.
Liverpool and Real have met only once previously in the competition, when the English side triumphed 1-0 in the final in Paris in 1981.
They have gone on to be crowned European champions five times in all - including two final victories in May's final venue the Stadio Olimpico.
"It's a mouthwatering tie and we are relishing it," Liverpool club secretary Bryce Morrison told Sky Sports News.
"We haven't played them in the competition since Paris so we are really looking forward to it."
Inter's game against United brings the Italian club's manager Jose Mourinho back to Old Trafford, where his Porto team knocked out United en route to winning the competition in 2004.
Mourinho said yesterday that he hoped to get United in the draw.
Ranieri's return to Stamford Bridge also adds spice to Chelsea's game against Juventus.
"For him (Ranieri) it means something different than for the rest of us," said Juventus sporting director Alessio Secco, who said he was confident of progress.
"When we were drawn with Real Madrid and Zenit in August we thought it was almost impossible but we won the group."