Chelsea will face Benfica in the Champions League quarter-finals, while holders Barcelona lock horns with AC Milan in a blockbusting last-eight showdown.
Roberto Di Matteo's Blues were paired with the Portuguese giants in Friday morning's draw in Nyon.
Barca meanwhile will face Arsenal's conquerors Milan in a mouthwatering confrontation for the right to meet Benfica or Chelsea in the semis.
Surprise package APOEL Nicosia get the reward of a quarter-final with the mighty Real Madrid for making it through to the last eight.
The winner of that tie will face either German giants Bayern Munich or French side Marseille, who clash in the other quarter-final.The draw keeps alive the tantalising prospect of Chelsea facing their former boss Jose Mourinho in the final in Munich.
Chelsea caretaker manager Di Matteo said: "When you get down to the last eight teams, any draw is difficult.
"I've seen Benfica many times. They were in Man United's group.
"It's a tough game for us.
"I think the fact that we play the first game away for us is good."
Di Matteo refused to contemplate a potential semi-final against Barcelona.
"Are you writing off AC Milan straight away, as easy as that - the leaders of Serie A?" he said.
"(We will take it) game by game. That's what I've learnt in my playing career and my coaching career."
Despite facing the competition's underdogs in the next round, Real club director Emiliano Butragueno is not prepared to underestimate APOEL.
"We have to be extremely respectful," he told Sky Sports.
"Of course on paper there were stronger teams that Apoel, but it is the quarter-finals and they are a very strong team."
Butragueno also refused to address the prospect of a Real-Barca final.
"The final is too far ahead," he said. "We have to be very focused on the next game and try to reach the semi-finals.
"That will be a difficult tie according to the draw. After that, if we are lucky enough to reach the final then we'll think about it."
AC Milan matched Barcelona at the Nou Camp in the group stage drawing 2-2, although they lost at home 3-2, and the club's director Umberto Gandini insisted they were confident.
He said: "At least it will be easy to organise the away game as we have been there recently and we know the place. We faced them in the group stage and the aggregate score was 5-4 so I think it will be balanced.
"We drew 2-2 there and played well also at home despite losing 3-2, so we have confidence because I think we have also improved since then."
He added: "It's a game every player dream to play, both teams will be very motivated and we will see the winner of Benfica-Chelsea in the semi-finals!"
Quarter-finals
APOEL v Real Madrid
Marseille v Bayern Munich
Benfica v Chelsea
AC Milan v Barcelona
Semi-finals
Marseille/Bayern Munich v APOEL/Real Madrid
Benfica/Chelsea v AC Milan/Barcelona
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