Winterburn joined Arsenal from Wimbledon in 1987 in a contract price £350,000. English left-back went on to make over 400 games for the Arsenal, helping the club win two FA Cups and three league titles.
Winterburn is rated as one of Arsenal’s greatest defenders, but he has announced he almost signed for Chelsea instead in the late 1980s.
‘I don’t really talk about it a lot, but two weeks before that [signing for Arsenal] I had gone to Chelsea for talks,’ Winterburn told the Football Ramble Daily podcast.
‘They wanted to sign me but that all fell apart.’
Asked why his transfer to Chelsea fell through, Winterburn responded: ‘I have no idea. I tend to find with me, that with life if things don’t go well, the best way to deal with it is to block it out.
‘Maybe I asked for too much money! A few days after that they signed Tony Dorigo, so they were obviously eyeing up us both, and maybe he was the better option at the time.’
English defender made two games for England after appearing as a star at the Gunners but never started a fixture for his country.
On his short international career, Winterburn added: ‘I think I knew all along my journey in professional football, and particularly when playing for Arsenal, that I wasn’t going to get a lot of caps for England.
‘I’m so proud of making two appearances, one for 20 minutes and one for 45 minutes. They’re still caps for England that some people would dream about.
‘I always say, when people ask about regrets, if I could have just started one game for England, that’s what I wanted to do, just to show, I was good enough to play.’
Winterburn’s former club the Gunners are currently third in the Premier League and face Sheffield United this weekend.