Dimitar Berbatov
Dimitar Berbatov broke the hearts of Spurs supporters when he insisted on moving to Manchester United at the beginning of the 2009-09 campaign.
While the money Tottenham received-£30.75 million-was a significant increase on their outlay of £10.9 million for the player, Berbatov’s genius was hard to replace.
The forward scored 27 goals in 70 league games for Tottenham, winning the league cup in 2008.