The 5 worst signings in Real Madrid's history

3. Jonathan Woodgate

Jonathan Woodgate's Real Madrid debut is considered one of the worst of all time

One of numerous highly-rated English central defenders produced in the early 2000s, Jonathan Woodgate’s move to Real in the summer of 2004 for a fee of £13.4m came as a surprise. It wasn’t that Woodgate didn’t have talent, more that the England international simply couldn’t seem to stay fit; he’d managed just 18 league games for Newcastle in his previous season.

It came as no shocker then when it was revealed that the Middlesbrough-born defender was actually injured at the time of his transfer to the Bernabeu, and so his first season ended with him failing to make his debut for Los Blancos, as he spent the entire time in the treatment room.

When he finally did make his debut – in a September 2005 match against Athletic Bilbao – things couldn’t have gone any worse. Woodgate scored an own goal in the first half and was then dismissed for a second booking midway through the second half. His performance has often been labelled as the worst debut match of all time.

Woodgate did eventually recover somewhat and established himself as one of Real’s better defenders, but his injury issues just wouldn’t go away and he ended the season with just 16 appearances in all competitions before being sent on loan to his hometown club of Middlesbrough in the summer of 2006. The move was made permanent the following summer, meaning the Englishman left Real with only a handful of appearances to his name – making his time at the Bernabeu an unmitigated disaster.