1. Cristiano Ronaldo (Manchester United to Real Madrid, 2009)
Bought for: £15m Sold for: £80m Profit: £65m

Cristiano Ronaldo of Real Madrid prepares to take a free kick during the La Liga match against Sporting Gijon in 2011 (Getty Images)
Exactly 23 days after Kaka’s arrival, Madrid broke the record for transfer fees again when they landed Cristiano Ronaldo from Manchester United for a mind-numbing £80m. In 2003, Ryan Giggs, Paul Scholes and a few other seniors urged Sir Alex Ferguson to shell out £15m to buy the youngster from Sporting Lisbon, after an inspiring performance against the Red Devils in a friendly.
6 years later, when the Gaffer was convinced that one of his favourite son’s thoughts were set on a move to Madrid, he extracted a huge fee as a compromise ringing in a profit of £65m, making it the most profitable deal to date.
Perhaps until ‘Los Blancos’ do a deal for a certain Gareth Bale!