Man United was drawn Friday to face the five-time champions, who beat the storied English club in the 2009 and 2011 finals.
The Blues also knockout out Liverpool in the next season's quarter-finals (7-5 - after that engrossing 4-4 second-leg), while the club's most recent showing was last season when they beat Man City in the last-8, but would go on to lose out to Real Madrid in the Final.
There is no seeding or country protection in the Champions League quarter-final or semi-final draw. Should Jurgen Klopp negotiate a home clean sheet win over Porto in the first leg, even better for their title odds.
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Meanwhile, Manchester United face another monumental task after their Paris Saint-Germain comeback, having drawn Barcelona in the most mouth-watering game of the draw.
Barcelona defender Gerard Pique also played in the two finals against Man United, where he spent four years early in his career.
"In accordance with paragraph 21.01 (b) of the UEFA Champions League regulations, the UEFA administration will determine which matches will be played on Tuesday, which matches on Wednesday".
Ajax will play Juventus in a rematch of two previous finals. Chelsea is especially happy that its draw of Slavia Prague, who it will not overlook, allows it some flexibility with the Liverpool league fixture sandwiched in between.
And Juventus' meeting with Ajax will be a rematch of the 1996 Champions League final at Rome's Stadio OIimpico, a match that the Italians won via a penalty shootout.
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Elsewhere Ajax pulled off a major shock by dumping out the holders Real Madrid while Porto saw off last season's semi-finalists Roma to earn their place in the draw.
The draw will be shown live on BT Sport 2.
Chelsea, meanwhile, needed a last-gasp equaliser to avoid defeat at home to Wolves last weekend, but this is a chance for the Blues to boost their top-four hopes as their three closest rivals in the table are not in league action this weekend.
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