1) Real Madrid – Jonathan Woodgate
Yes, Jonathan Woodgate was a Real Madrid player. I promise you I wiki’d it before putting his name on this list. Woodgate spent two whole seasons at Los Blancos where he played 9 games scoring no goals.
Madrid paid £13.4 million for the Englishman but they realised too late that they had overpaid. They should've seen the warning signs or at least taken a look at his injury record before paying Newcastle that amount of money.
But it was a period of financial strength for Madrid and they wanted to use that to their full advantage. Even so, recruiting a player like Woodgate had all sorts of red flags even before the move had materialized.
Woodgate ended up making only 9 appearances in two years at the club scoring zero goals. He will probably go down as the worst transfer ever witnessed in Spanish football