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#8 Jonathan Woodgate-2004
Jonathan Woodgate, who is currently signed to Middlesbrough, is considered as one of the worst signings in the Real Madrid's history till date because of his transfer fee of £13.4 million, which proved to be a complete waste of money for the giants.
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Despite the injury issues Jonathan Woodgate had in past, he had proven himself as the best defender in England during his stay with Leeds and Newcastle United. However, it was a bit of a surprise when Spanish giants came knocking on his door and signed him in 2004 (Woodgate was actually injured at that time).
Unfortunately, things didn't go well for Woodgate after his signing with the club, as he continued to have serious injury problems and all of this led him to not feature in any of the matches played by Madrid in 2004.
After almost a year he played his first game for the Madrid against Athletic Balboa in 2005 scoring a goal though it didn't make much of an impact.
After showcasing his skills as a defender his injury issues struck again which led Madrid offloading him first on loan than on a permanent transfer to Middlesbrough.
He left Madrid the following year for a reported fee of £7m, signing a four-year deal with the North-East club before making his final move to the Spurs.
