6. Jo (Manchester City to Internacional, 2011)
Bought for: £18m Sold for: free Loss: £18m
Jo was a club record signing at about £18m when City bought him in 2008. Sadly, the valuation and his talent never really matched and he was shipped back to Brazil in 2011 for free. He is now back in the reckoning though at the national level after being part of Luiz Felipe Scolari’s Confederations Cup squad.
5. Emmanuel Adebayor (Manchester City to Tottenham Hotspur, 2013)
Bought for: £25m Sold for: £5m Loss: £20m
Another of the Man City loss making products, Adebayor was found out soon enough at City who realized that he wasn’t really the big-time player that they needed. After loan spells at Real Madrid and Tottenham, Spurs decided to make the Togolese’s move permanent by signing him for £5m last year.