Holders Inter Milan
will tackle Schalke, while 2009 winners and favourites for this season's tournament Barcelona have been paired with Shakhtar Donetsk.
In a repeat of the 2008 final between the Premier League giants, Chelsea and United will lock horns for the chance to reach the semi-finals of this season's Champions League.
Carlo Ancelotti, who has tasted European glory as AC Milan coach, must overcome a domestic rival if he is to maintain owner Roman Abramovich's dream of Champions League success for Chelsea.
The Blues beat United 2-1 at Stamford Bridge in the Premier League earlier this month and have not given up hope of reeling in the current leaders.
The first leg of the quarter-final tie at the start of April will be held in West London, with the return at Old Trafford a week later.
Whoever comes through that two-legged encounter will meet either Inter or Schalke in the semi-finals for the right to secure a place at Wembley.
Tottenham, meanwhile, have been handed a mammoth task to reach the final of the competition after being drawn with Real Madrid in the last eight.
Harry Redknapp's side have already knocked out one European heavyweight in the competition after edging past AC Milan in the last 16.
The tie will also see a return to England for Real coach Jose Mourinho, who guided Inter past Chelsea en route to lifting the trophy last season.
Real will entertain Spurs at the Santiago Bernabeu in the first leg and there is certain to be a raucous atmosphere at White Hart Lane in the return meeting.
If Spurs overcome Real, then Barcelona could await in the semi-finals after Arsenal's conquerors were paired with Shakhtar Donetsk.
Ukrainian side Shakhtar are in the quarter-finals for the first time and are the menacing dark horses in the competition due to their formidable home record.
Barcelona are at home in the first leg and will be hoping to build an advantage to take to Shakhtar for the second leg.
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