#5 Jonathan Woodgate
A somewhat surprising signing for Real Madrid in the summer of 2004 – the same period that saw Michael Owen move to the Bernabeu – central defender Jonathan Woodgate moved to the club from Newcastle for a hefty transfer fee of just over £13m.
The move was always considered a risk due to Woodgate’s injury issues – he only made 18 league appearances during his last season at Newcastle – and was in fact injured at the point in which he signed for Los Blancos.
Woodgate’s first season in Spain was an absolute disaster; he didn’t make a single appearance for Real due to his injury issues, and had to wait until September 2005 to appear for his new side in a league tie against Athletic Bilbao.
When he did, things went from bad to worse. In one of the worst debuts in football history, Woodgate scored an own goal and was later sent off, although Real did go on to win the game 3-1.
Eventually Woodgate did force himself into Real’s first team, but his issues with injuries quickly rose their head again and a back problem restricted him to just 14 appearances in all competitions in 2005/06 before he was sent to Middlesbrough on loan – a move he made permanent in the following summer.
That summer saw Woodgate voted as Real’s worst signing of the 21st century, basically summing up his torrid time in Spain.