6. Jimmy Floyd Hasselbaink
Joe Giddens/EMPICS SportJimmy Floyd Hasselbaink's decision to leave Chelsea was as ill-timed as any departure you're ever likely to see. In 2004, the striker called time on his Blues career, despite the fact Roman Abramovich's revolution at the club was just picking up a head of steam. Hasselbaink moved to Middlesbrough with bold claims
the club could qualify for the Champions League, and though that didn't come to fruition, he did lead Boro to the 2005-05 UEFA Cup Final. Having won only the FA Charity Shield in his four years with Chelsea, however, Hasselbaink must have been gutted in 2005 as he watched his former colleagues win their first Premier League title since 1955. The forward later admitted to the BBC that
he felt he could have made a contribution to that title-winning side.