Raul Meireles – £12 million
A surprise transfer, Meireles arrived under Andre Villas-Boas in the 2011 summer window for a fee believed to be around £12 million.
News of the transfer was given a mixed reaction from Chelsea fans, particularly on occasions when he was selected ahead of Frank Lampard.
To brand Meireles a total flop would be inaccurate; he had his moments as a Chelsea player (think Benfica in the Champions League), but was too inconsistent for a place in the Chelsea starting line up despite some good performances.
Despite becoming a champion of Europe he was sold by Roberto Di Matteo, just after the British transfer window closed, to Turkish side Fenerbache.
The player signed from Liverpool was never really given a full crack of the whip, but as we sold him for a loss he goes down as a slight deadline day flop.