1. Jonathan Woodgate (Real Madrid)
After impressive spells at Leeds United and Newcastle United, Woodgate was signed by Real Madrid in 2004 for a fee of £13.4 million, the price surprising many given Woodgate’s physical frailties and injury frequencies.
Due to a long-term injury, Woodgate was not able to play a single match in his first season for the Spanish giants, and made his debut in September 2005 in La Liga against Athletic Bilbao. However, his opening game could not have gone worse, as he scored an own goal, and then was red-carded.
More injuries curtailed his Madrid career, as Woodgate left for England in 2006 after playing just 9 league games for Los Blancos. He was also voted the worst signing of the 21st century by Spanish daily Marca.
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