Darren Anderton told Goals on Sunday he regrets passing up the chance to join Manchester United in the mid-nineties.
The former England winger remains a Tottenham hero after spending 12 years of his career at White Hart Lane, but he held talks with Sir Alex Ferguson in the summer of 1995 over a switch to Old Trafford.
Anderton, who was one of the hottest properties in English football at the time, was persuaded to sign a contract extension by Spurs owner Sir Alan Sugar and says he enjoyed his time in North London.
But he regrets not becoming part of the team that won the treble in 1999 and competing for a place in a midfield that included the likes of Ryan Giggs, Roy Keane, Nicky Butt, Paul Scholes and David Beckham.
Anderton told Goals on Sunday: "I had a clause in my contract that basically sad that for a figure I was able to go and United and Blackburn, who were the champions that summer, came up with that.
"I spoke to Sir Alex on the phone, which was a bit daunting I suppose, and he sold the club, although he didn't have to. I said I supposed it was a possibility. Why not?
"I then went to Sir Alan Sugar's house the following day and he didn't really let me leave without signing a new deal!
"I was 23 and I didn't want to leave. Things had gone great and when I first went to Spurs they were loyal to me; I struggled in the first six months. I didn't see it as the right time to move on.
"The following year was Euro 96 and I wanted to be part of that. If I went to United and struggled or didn't settle, as I could have done, then maybe I'd have missed out on that.
"I regret not being part of that team that went on and did great things. It would have been great to have been part of that team and to have played under Sir Alex Ferguson, but I think I was lucky to play for Spurs for 13 years."