Tough CL draws for Prem pair
Man City have been drawn against Barcelona, while Arsenal will face Bayern Munich following the draw for the Champions League round of 16.
Arsenal, the Premier League leaders, were beaten by Bayern at the same stage last year, and have paid a heavy price for a final-day defeat at Napoli which relegated them to runners-up in their group.
And Manchester City, who finished second to Bayern in their group, have been similarly punished with a last-16 draw against Barcelona.
City's draw is all the more galling given the circumstances: needing a two-goal victory at Bayern to finish top, Manuel Pellegrini's misreading of the mathematics led him to defend a 3-2 lead rather than chase a fourth goal.
Elsewhere Chelsea will be up against Galatasaray and Didier Drogba, the man whose penalty won them the competition in 2012.
And Greek champions Olympiakos stand between Manchester United and a place in the quarter-finals.
City's director of football Txiki Begiristain, who joined the club from Barcelona, admitted the draw "could be maybe better".
But he told Sky Sports News: "For the people it's a great, great match. Two big teams, one with a lot of history, the other a new one also trying to win the trophy and be there in Europe.
"And the game in Munich, winning against the champions, will give us a lot of confidence going away to Barcelona.
"The way that we are playing, we're showing we can score in all matches. This is the most important thing in the Champions League."
Elsewhere, seven-time winners AC Milan will face Atletico Madrid, Bayer Leverkusen must face Ligue 1 champions Paris Saint-Germain, Schalke will play Real Madrid and Zenit St Petersburg have been paired with Borussia Dortmund.
Champions League Round of 16 draw:
Manchester City v Barcelona, Olympiacos v Manchester United, AC Milan v Atletico Madrid, Bayer Leverkusen v Paris Saint-Germain, Galatasaray v Chelsea, Schalke 04 v Real Madrid, Zenit St Petersburg v Borussia Dortmund, Arsenal v Bayern Munich.
First legs to be played: 18/19/25/26 February 2014.
Second legs to be played: 11//12/18/19 March, 2014.