7. Darren Huckerby
After three excellent years at Coventry City, Darren Huckerby found himself targeted by a number of high-profile clubs and in the summer of 1999, he made the decision to join Leeds United.
The attacker would have had high hopes of helping the club build on their fourth-place finish in the standings the previous year but while Leeds would go on to become Champions League semi-finalists within two years, Huckerby spent much of the transition on the sidelines.
Despite costing a reported fee of £6m, Huckerby made just 14 starts in all competitions during his season-and-a-half at Elland Road. He made a further 43 appearances from the bench but it wasn't what he had in mind when he looked to take the next step of his career.
Huckerby did have a couple of positive moments - most notably a goal in the Champions League against Besiktas - but all in all, he endured a disastrous time in Yorkshire and would eventually be sold to Manchester City.
He would still enjoy a respectable stint in English football but his best form came at the second tier where he won the First Division title with both City and Norwich City.