When he passed the medical to sign for Real Madrid, Toon chairman Freddy Shepherd later said: "I couldn't believe it".
He rarely played in Spain, and when he returned to England he had an interview with then-Toon boss Glenn Roeder, and Woodgate said: "I signed for Boro rather than Newcastle because all Roeder talked about was my injuries."
Now there is a serious threat the former England international could be forced to hang up his boots.
Tottenham boss Harry Redknapp has raised concerns over Woodgate's groin injury and admits he has no idea when his centre-back will be fit again.
Woodgate, 29, suffered with the complaint last season and travelled to Germany for an operation in August but the problem has not gone away despite a recent injection for the injury.
The former Real Madrid defender has only completed two games this season, the recent Premier League wins over Sunderland and Wigan, but is back on the sidelines again.
"He's had the injection but it doesn't seem to have done the trick really," Redknapp said.
"I don't know if he can have another operation, he's had so many. I don't know what the next step is really.
"It's a shame, he's such a good player. When he's fit he's fantastic for us but he is struggling a bit at the moment again.
"It's difficult. Some people want to inject it, others want an operation. It's very hard to find with an injury like that, to get to the bottom of it all.
"There's no light you can see. With a broken ankle or whatever at least you know what you're dealing with. But these injuries can drag on forever."