1. Gareth Bale
Bought for: £7m by Tottenham Hotspur on 25.05.07
Sold for: £85.3m by Real Madrid on 01.08.13
Tottenham Hotspur fans may miss Gareth Bale but drove without question the hardest bargain in transfer history when Real Madrid came calling for the Welsh wing wizard last summer, securing a world-record £85.3m fee before allowing him to become the latest La Liga star.
Bale's reported £7m fee that took him from Spurs to Southampton to 2007 should have been far more profitable for the South Coast club, but their decision to eventually waive a 25% sell-on clause now looks like an absolute disaster despite easing their financial woes at the time.
The likes of Paris Saint-Germain and Monaco may be filthy-rich but are mere pretenders to the throne when it comes to extortionate transfer fees, with Madrid firmly keeping their place at the top of the transfer tree.