First of all, it should be noted that Florent Malouda, signed by Mourinho in 2007 for £13.5 million, has had a trophy-laden Chelsea career, having won the Champions League, the Premier League title and three FA Cups. He was also voted the clubs players player of the year in 2010. But it is with a great degree of sadness that the former Lyon man makes number 7 on our list of worst ever Mourinho signings. Despite featuring in the squad that won the Champions League against Bayern Munich last season, Malouda was completely omitted from all of Roberto Di Matteo's squads this season and hasn't made a single appearance for the Blues since last May. He has since been ordered to train with the reserves and will almost certainly be leaving Stamford Bridge at the end of the summer when his Chelsea career ends in indignation.