Retour
The former Scotland international moved to the Premier League after a prolonged January transfer saga but now wishes he had stayed at Ibrox until the end of the campaign.
Hutton said: "I don't tend to look back on my career and think 'what if' or if I'd done something different; I'm happy with the way it panned out. [FootballPredictions.com]
"But it's probably the one thing for me, leaving Rangers in January 2007. I should have stayed till the end of the season."
He also mentioned the pressure he was under from both sides, Rangers and Tottenham, which largely influenced his decision. "But looking back now, I think if I'd stayed till the summer, of course, Rangers got to the Europa League final as well that season.
"It would have been something I'd have played in at Manchester City as well. So it would be something that I would have loved to have been part of. So it's probably one of the only things that I look back on and think maybe I could have changed that," he added.
Hutton also revealed how close he came to rejecting Tottenham altogether, during a transfer saga that lasted almost the entire month.
At one stage, the defender refused to board a plane that had been arranged to take him south as he insisted he would not leave Rangers. "I mean, it went on for pretty much the whole of January. I was getting told I had a plane arriving to take me down. I didn't turn up for it.
"I was saying no at one stage, like, 'That's it, absolutely not, I'm not going.' But yeah, I wish I'd just waited until the summer," said Hutton.
He further added that he was ultimately swayed by conversations with Daniel Levy and the opportunity to play in the Premier League.