The winger, who has struggled since joining Tottenham in 2008, revealed to Goal.com that he was close to joining Major League Soccer.
Bentley has struggled since joining Tottenham in a big-money transfer worth 16 million pounds in 2008. The winger has only made 42 appearances in four years with the club and has gone on loan to Birmingham and West Ham.
There were reports in May that he was close to joining Tottenham's affiliate club, San Jose, on a season-long loan.
While the former Arsenal youth product did not mention the MLS team that was interested, he confirmed that a move to the North American league almost happened.
"Yeah, it was an opportunity that fell through," Bentley told Goal.com. "It's a great country, it was a great city. The league is developing. Hopefully, one day in the future [there will be another opportunity to play in MLS]."
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Prior to his move to White Hart Lane, Bentley was a rising star with Blackburn Rovers. In his final season with the club, he had six goals and 11 assists in league play. He excelled at crossing the ball and in set piece delivery. Some speculate that Bentley's dip in form was a result of the pressure of living up to the hefty price that Spurs paid for him.
A loan move to America, especially in a small market like San Jose, could have paid dividends for the 27-year-old. It would have also been intriguing to see how MLS leading goalscorer Chris Wondolowski would have fared receiving service from Bentley.
Maybe next year...