Bought for: £32.5m by Manchester City in 2008
Sold for: £16m to AC Milan in 2010
Manchester City's attempt to underline their new-found financial muscle with a marquee led to the deadline-day purchase of Robinho in 2008, a move widely heralded as a strong if over-priced piece of transfer business.
Robinho briefly flirted with the status of City in impressive early performances but interest from the Brazilian forward soon waned, leading to a swift exit from the Etihad in a half-price sale, with AC Milan deciding they could revitalise his flagging career.
In truth Robinho has never been able to recapture the form that led Real Madrid and City to both shell out big bucks for his services, as Milan now face up to the prospect of taking a similar hit to the one suffered by City in 2010.