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Fiorentina, despite being amongst the top seeds for the draw, have been drawn with German giants Bayern Munich, who eliminated Juventus after crushing them 4-1 in the group stage.
Elsewhere in the draw holders Barcelona will face Stuttgart, their Primera Liga rivals Real Madrid face a tricky tie against Lyon and Arsenal meet Portuguese champions Porto.
Bordeaux were drawn with Olympiakos and Sevilla play CSKA Moscow in the remaining ties.
For the first time this year, the fixtures in the last 16 will be held over four weeks and eight days with the first leg ties to be played on 16/17/23/24 February and the return matches on 9/10/16/17 March.
UEFA Champions League 2009-10
Round of 16 First Leg
Tuesday 16 February 2010
Lyon v Real Madrid (1945)
Milan v Manchester United (1945)
Wednesday 17 February 2010
Bayern Munich v Fiorentina (1945)
Porto v Arsenal (1945)
Tuesday 23 February 2010
Olympiakos v Bordeaux (1945)
Stuttgart v Barcelona (1945)
Wednesday 24 February 2010
CSKA Moscow v Sevilla (1730)
Inter v Chelsea (1945)
Round of 16 Second Leg
Tuesday 9 March 2010
Arsenal v Porto (1945)
Fiorentina v Bayern Munich (1945)
Wednesday 10 March 2010
Manchester United v Milan (1945)
Real Madrid v Lyon (1945)
Tuesday 16 March 2010
Chelsea v Inter (1945)
Sevilla v CSKA Moscow (1945)
Wednesday 17 March 2010
Barcelona v Stuttgart (1945)
Bordeaux v Olympiakos (1945)
Source: UEFA
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