4) Claude Makelele – £16.8m (2003)
Age of transfer: 30
Makelele’s contribution to the game is for all to see as he is the only player to have a position named in his honour.
His arrival in the summer of 2003 can be viewed as the most important purchase in the Roman Abramovich era as it kick-started Chelsea’s successful period.
3) Diego Milito – £20m (2009)
Age of transfer: 30
Paying £20million for a 30 year-old seemed like an odd decision from Mourinho in summer 2009, but after Milito scored a brace to win the Champions League for Inter that season, it reminded the world to never question the Portuguese boss.