4: Shaun Wright-Phillips
The in-demand England international arrived at Chelsea from Manchester City in the summer of 2005 for an eyebrow-raising fee of £21m, and it is fair to say that the wide man never truly managed to live up to his hefty price tag during his time at the Bridge.
SWP, the step son of former Arsenal legend Ian Wright, was given plenty of opportunities to display his talents on the wing in west London, however, after three years of a stop-start career with the Blues, the Englishman eventually re-joined City in August 2008 for only £8.5m.
3: Steve Sidwell
Another Bosman-free disaster by manager Jose Mourinho, with the Englishman being signed from Reading in July 2007 in what was one of the self-styled ‘Special One’s’ final-ever pieces of transfer business during his first spell in charge of the Blues.
But, after just 15 Premier League outings and no goals, the midfield player was then sold to Aston Villa for £5m the next summer.