14) Jimmy Bullard (Fulham to Hull City – £5m – 2009)
The Tigers were hoping that the flamboyant midfielder would help them maintain their Premier League status, paying him approximately £50,000 a week for the privilege, but it didn’t go to plan.
A longstanding knee injury flared up on his debut and he only played 24 games for Hull over three seasons. He was loaned to Ipswich Town before he eventually left on a permanent basis.