9. Alberto Aquilani –Â ÂŁ13 million Loss
Number 9 in the list is Alberto Aquilani.
Currently playing for Italian side Fiorentina in Serie A, Aquilani makes the list after Liverpool splashed out £20million on signing him from AS Roma. However, after failing to impress during his time at Anfield, the Premier League side then sold him back to Italy for just £7m.
Liverpool made a loss of £13 million after selling him back in 2012.