The Spurs boss has revealed that the England international is set to have one final operation in a last ditch attempt to save his career.
Woodgate moved to White Hart Lane in 2008 from Middlesbrough but only made three appearances last season for the club.
The defender has been plagued by injury problems throughout his career since making his Premier League debut in 1998 with Leeds United.
The player’s ability has never been questioned and he has long been viewed as one of the most naturally gifted defenders in the country, an accolade highlighted in 2004 when Real Madrid purchased the player for just over £13 million.
However, he only featured in 9% of Madrid’s games during his two-year stint at the Bernabeu, and a similar injury record in the last year at Spurs has prompted talk of retirement at the age of just 30 years old.
“It’s so sad for Jonathan because he is such a good player and a great lad,” Redknapp said.
"They're talking about having an operation for Jon now. That's his last chance.
"Well, probably. His last resort, I think, will be an op.
"If he has the operation he will be out for quite a long time, but we'll back him 100%, we just hope he can get it sorted."
Woodgate is expected to travel abroad for the procedure, having already visited surgeons in America and Australia in a bid to cure the ongoing problem.
"Someone abroad's going to do it. The physio's taken him," Redknapp added.
"He's been all around the world looking for a cure."Meanwhile, Redknapp revealed that Spurs will be without their midfield ace Luka Modric for tomorrow’s crucial second leg against the Young Boys in the Champions League qualifier.
The Champions League hopefuls trail 3-2 to the Swiss side and know that only a victory will see them through at White Hart Lane, but they must now do it without their talismatic playmaker.
The loss of Modric isn't going to derail the club's Champions League ambitions though, according to the Tottenham manager.
"Luka Modric is not fit, but the other lads came out and joined in training, so hopefully they'll be okay. We'll wait to see if they have any reaction," Redknapp told the club's official website.
"Luka's a top player, a fantastic player, but we've had to play without him before.
"We had a long spell last season when he was out and we coped okay. We were without him at Stoke on Saturday as well and we were outstanding. It was a great to go and win there."