The former France international made his name in England during a six year spell in London, split by a season at Barcelona, and was often linked with a move to the Red Devils.
Petit joined Arsenal in 1997, where he was reunited with his former Monaco boss Arsene Wenger. Following an unsuccessful spell at the Nou Camp, he opted for a move to Chelsea in 2001, over Manchester United.
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The former midfielder went on to make 75 appearances for the Stamford Bridge club, during a four-year spell, but has spoken of his regret about choosing West London over Old Trafford.
During an interview with Yahoo France, the 1998 World Cup winner said how his decision to join the Blues was for personal reasons and not a football decision.
The 44-year-old said: "I was very happy at Arsenal, I listened to my heart rather than reason. I blamed myself afterwards.
"Manchester United saw the state I was the first month in Barcelona. I enjoyed the process of Ferguson.
"If I had to choose a sport, I would have gone to Manchester rather than Chelsea. But once again, I preferred a private choice on a sports choice. I regret."
Despite being a key figure in the Chelsea midfield, Petit was unable to claim any silverware during his time at the Bridge, and watched on as Man United won the Premier League and FA Cup.
Had the Frenchman taken the opportunity to join the Red Devils, he would have shared the midfield with players like Paul Scholes, Roy Keane, Nicky Butt and Juan Sebastian Veron, enough to wet the appetite of most United fans.
Chelsea supporters will not be happy to hear one of their former star player regrets turning down their Premier League rivals, but can be grateful for the influence Petit had at the Bridge.
He helped the club qualify for the Champions League for only the second time in their history, before missing the majority of his final campaign through injury.