Chelsea will have to overcome Benfica if they are to set up a possible Champions League semi-final with Barcelona and a chance to erase one of the most painful moments in the club's history.
Benfica, who drew home and away with Manchester United earlier this season as they topped their group, will be no pushovers but the enticing prospect of a Barcelona semi-final is hovering in the background.
Chelsea lost out to Barcelona in the semi-finals in 2009 when Andres Iniesta scored in injury time at Stamford Bridge to seize a place in the final for the Catalan side.
Roberto Di Matteo, the club's caretaker manager, refused to even contemplate such a meeting - pointing out that Barca have their hands full in the quarter-finals after being drawn against AC Milan.
In the other quarter-finals, Real Madrid were drawn against Cypriot side APOEL while Marseille will take on Bayern Munich.
The draw also means there is a good chance of the ultimate El Clasico happening - a mouthwatering all-Spanish final between Real and Barcelona.
Di Matteo said: "When you get down to the last eight teams, every draw is very difficult.
"I've seen Benfica many times. They were in Man United's group and they are a tough opponent for us.
"I think the fact that we play the first game away from home is good, a little bit like the Napoli game."
In response to a possible meeting with Barcelona, Di Matteo added: "Are you writing off AC Milan straight away, as easy as that - the leaders of Serie A?
"It's game by game. That's what I've learnt in my playing career and managing and coaching career."
Chelsea, England's last remaining club in Europe, have two former Benfica players in their squad - the Brazilians David Luiz and Ramires.
The Portuguese club are currently second in their domestic league, a point behind Porto, and overcame a 3-2 first-leg defeat by Zenit St Petersburg in the first knock-out stage, winning 2-0 at the Estadio da Luz to secure their place in the quarter-finals.
Chelsea's old guard came to the club's rescue against Napoli on Wednesday night with John Terry, Frank Lampard and Didier Drogba all scoring in a 4-1 win, and the club's chief executive Ron Gourlay said a blend of experience and youth was vital.
He told the club's website: "You need experience, you need youth and you need a little bit of luck.
"Any team that has won it will tell you this, hopefully we get that but let's worry about Benfica, give them the respect they deserve and take it from there.
"Robbie [Di Matteo] and everyone around him, the players, we all have to play our part.
"He has started well in three games and everybody knows the objectives until the end of the season. Everybody is clear on what we want to achieve and everybody is pulling in the same direction.
"The competition is very important to us, being in the Champions League is very important and we want to make sure we are in the competition next year."
AC Milan, however, 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 dreams to play, both teams will be very motivated and we will see the winner of Benfica-Chelsea in the semi-finals."
APOEL Nicosia v Real Madrid
Marseille v Bayern Munich
Benfica v Chelsea
AC Milan v Barcelona
First legs to be played on March 27/28. Second legs to be played on April 3/4.
Marseille/Bayern Munich v APOEL Nicosia/Real Madrid
Benfica/Chelsea v AC Milan/Barcelona
First legs to be played on April 17/18. Second legs to be played on April 24/25.