#2 Jonathan Woodgate
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Apart from one of the worst, Jonathan Woodgate would also go down as one of the strangest signings Real have ever made in their past. Despite his poor fitness record and absence on the pitch due to recurring injuries, the Englishman found himself in the dressing room at Santiago Bernabeu as Los Merengues forked out £13.4 million to sign him from Newcastle.
Needless to say, the decision backfired rather horribly. Woodgate scored an own goal on his debut against Athletic Bilbao, eventually being sent off in the fixture. At one point, he did establish himself as a regular starter for Real Madrid, but injuries wrecked his chances of becoming a great player at the club.
After 3 seasons, 14 appearances and a loan move to Middlesborough, Woodgate left Real Madrid with just one goal to his credit.