Roberto Di Matteo

This dynamic midfield player endured a roller-coaster time in the year 2000 - battling his way back into first-team contention following a serious ankle injury and a fractured arm, scoring the winning goal in the FA Cup Final and dominating the midfield in Chelsea's exciting Charity Shield triumph. With the sale of Didier Deschamps and Dan Petrescu he seemed poised to reclaim his favoured central midfield position but shortly after Gianluca Vialli's shock departure as Chelsea manager the fates dealt Robbie a terrible blow. During the catastrophic UEFA Cup defeat at the hands of Swiss club St Gallen in September he suffered a badly broken left leg and this brought his season to a premature close. He was sorely missed for his steadying influence and drive in midfield and in his absence the team plunged from being Premiership contenders to a position of mid-table obscurity. The fact that Chelsea have won six major trophies since Robbie's arrival in July 1996 after years of under-achievement speaks volumes for his contribution to the club's transformation into one of the modern-day giants. Despite several operations on his injuries Robbie failed to recover and announced his retirement on 19th February 2002.