Klinsmann, who before Bale was the last Spurs player to score 20 league goals in a season and also win the prestigious Footballer of the Year for the feat, said Bale was a tremendous talent but he would need to play on the big stage with a club in the Champions League.
Klinsmann said that had been the reason he left the north London side with a heavy heart in 1995 for Bayern Munich right after winning the Footballer of the Year award.
"I'm a huge Tottenham fan and I'm also a huge Gareth Bale admirer," Klinsmann said in an interview near his home in Southern California.
"I just hope, and I'm keeping my fingers crossed, that they make into the Champions League. The risk is very big that if you don't go into the Champions League, you'll lose Gareth Bale."
Bale has scored 25 goals in all competitions for Spurs, many of them spectacular strikes from outside the penalty area.
His performances helped Tottenham reach the Europa League quarter-finals and have kept them in the race for a top-four finish in the Premier League and a possible return to the Champions League.
Spurs are currently fifth in the league, two points behind Arsenal who have played a game more, and a win over Chelsea on Wednesday would boost their Champions League hopes.
Bale's performances have also sparked widespread media reports that Spurs would value their prize asset at somewhere between 60 million pounds ($92.82 million)and 80 million pounds -- a price tag which would scare off all but the richest of suitors.
"I think he deserves that recognition, footballer of the year." Klinsmann said. "He deserves an amazing amount of admiration for how he's played the last two or three seasons.
"He plays for Wales and can probably never play in a World Cup. A player like him needs to play on the biggest stage. The risk is if Tottenham don't reach the biggest stage, the Champions League, that they might lose him."
Klinsmann said that was, ultimately, the reason he left Spurs in 1995 right after winning Footballer of the Year.
"My reason for leaving the Spurs was only to play on a bigger stage," he said.
"That's why I left the Spurs for Bayern Munich many years ago. I wanted to play top European football.
"That might be the risk now with Gareth. But I hope they make it happen, qualify for the Champions League and play Champions League next season and can keep Gareth Bale at White Hart Lane. That is my big hope."
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