He arrived at Newcastle in January 2003 from Leeds United for £9m, but a succession of fitness setbacks limited him to just 37 appearances in all competitions during the next season and a half.
Freddy Shepherd
That didn't put off Madrid, who signed Woodgate for around £13m 10 years ago today, despite the fact that he was suffering with a thigh problem at the time.
A German specialist at the defender's medical had claimed that the injury would clear up shortly, but that didn't prove to be the case.
Freddy Shepherd took the money, with a £4m profit, and it was a wise move - despite Woodgate being a popular figure on Tyneside.
We have had our injury disasters at Newcastle - Michael Owen being the most expensive - but Shepherd got one over on Real Madrid that day.
Speaking at the time, Newcastle manager Sir Bobby Robson said: "I don't blame Jonathan in a way because he's going to arguably the biggest club in the world, I think, at this moment.
"The power of Figo and Ronaldo, Zidane, then Beckham and now Owen. If you were in his shoes, what would you do? This is an extreme, exceptional offer which basically we had to take. No-one is pleased that he's gone because we know what we've lost. At his best, he's the best in the country."
The thigh injury that Woodgate arrived in Spain with ruled him out of the entire 2004-05 season, with his debut eventually coming in September 2005 against Athletic Bilbao. It was a game to forget for the 25-year-old, though, as he scored an own goal, before later being red carded.
He returned to score in a Champions League clash with Rosenborg, but injuries once again took hold and it came as little surprise when in 2006 when he was loaned out to Middlesbrough, whom he would join permanently 12 months later, having made just 14 outings for Madrid.
In 2007 he switched to Tottenham Hotspur, where he spent four campaigns and then moved to Stoke City. Two years ago returned to Middlesbrough and he remains at the Riverside to this day.