5. Dimitar Berbatov | €33 million loss
Tottenham Hotspur to Manchester United €38m
When Sir Alex Ferguson purchased the most expensive Bulgarian footballer of all-time in 2008, he certainly was not paying for a workhorse striker to form the first line of defence.
Instead, Berbatov brought a tranquil swagger so charming that he could be forgiven for his reluctant defensive attitude.
Not the quickest forward either, the former Bayer Leverkusen hitman relied on his composure and invention to fashion scoring chances.
From stunning bicycle kicks against Liverpool to despicable howlers versus Arsenal, the Bulgaria international produced moments of both genius and frustration in a red shirt.
Inconsistency is rarely forgiven at United, and thus Berbatov left Old Trafford for nearly an eighth of the figure paid for his arrival.
Manchester United to Fulham €5m
In 2012, the then 31-year-old signed a two-year deal at Craven Cottage. Considering his advancing age, the move to London was clearly a sensible one as the former CSKA Sofia striker scored 15 goals in his debut season for Fulham.