10) Wayne Bridge (Chelsea to Manchester City – £10m – 2009)
The England international had performed well at Chelsea, despite being Ashley Cole’s understudy at Stamford Bridge, but his switch to City didn’t go to plan.
Bridge was a regular starter for the first 18 months but manager Roberto Mancini dropped him for the start of the 2010/11 season. Despite earning £90,000 a week, he was loaned out three times before eventually leaving on a free transfer in 2013.