Jose Mourinho will have to overcome his former club Chelsea, if his current side Inter are to reach the last eight of the Champions League.
Another high profile reunion will see Milan’s David Beckham face his former club, Manchester United for the first time since leaving Old Trafford in 2003.
Holders Barcelona will be relatively pleased with their draw against struggling Bundesliga outfit Stuttgart, while big-spending Real Madrid will meet French side, Lyon, who are currently eight points adrift of Ligue 1 leaders Bordeaux.
Inevitably, much attention will be focused on Chelsea’s encounter with Inter, and in particular the second leg of the tie which will see Mourinho return to Stamford Bridge where he is still idolised after leading the Blues to back-to-back Premier League titles in 2005 and 2006.
Beckham’s first return to Old Trafford is equally noteworthy, with the England international’s loan move to Milan from LA Galaxy seeing him up against the club where he made his name.
England’s other representatives Arsenal will be hopeful of progressing to the quarter-finals having been paired with 2004 winners Porto.
Elsewhere, Bayern Munich, who produced a memorable victory away to Juventus to book their place in the last 16, return to Italy to face a Fiorentina side who enjoyed home and away victories over Liverpool.
CSKA Moscow are up against Sevilla, while French champions Bordeaux boasted the best record in the group stages and will be confident of further progress against Olympiakos.
Milan v Manchester United
Porto v Arsenal
Lyon v Real Madrid
CSKA Moscow v Sevilla
Bayern Munich v Fiorentina
Inter Milan v Chelsea
Olympiakos v Bordeaux
Stuttgart v Barcelona