2. Dimitar Berbatov
Bought for: £30.75m by Manchester United in 2008
Sold for: £4.75m to Fulham in 2012
Manchester United were left in a difficult position with Dimitar Berbatov last summer, attempting to claw back some of the substantial £30.75m spent on a player that while extremely talented had been a peripheral figure at Old Trafford for quite some time.
Berbatov finished his United career two shy of 50 Premier League goals, allowed to join Fulham at a staggering £26m loss with first-team opportunities extremely limited by the arrival of Robin van Persie.