Harry Redknapp has admitted that Jonathan Woodgate has just one last throw of the dice to save his career, while he is also worried for Ledley King.
The 30-year-old defender has been out for a year with a groin injury and operations in Australia and America have failed to provide a remedy.
Woodgate is poised to go abroad for yet another operation on an injury that has dogged him for eight years.
Should it fail, he may be forced to call time prematurely on his career.
"You can't treat it and this is his last chance," Redknapp told the Daily Star Sunday.
"We're going to give Jonathan every chance but it has been a year [since he played], and it'll be another year if he has another op."
Meanwhile, the Tottenham boss has expressed fears King could end up with serious problems if he keeps playing.
King, 29, is plagued by a knee injury that causes swelling after games, restricting him to just one appearance a week.
But Redknapp concedes he has to balance the desire of his captain to play, against his long-term health.
"It's something that we constantly talk about. I don't want him ending up a cripple," he added.
"Only Ledley knows how he feels. He says he's fine. He says he will know when he's had enough.
"He wants to play and while he feels good he'll keep going. Do I worry? In the long term I do. He might need a knee replacement down the line."