Now his delivery is just as important in his job as a postman for the Royal Mail.
Just over 30 years ago, Gynn and Coventry were celebrating after beating Tottenham 3-2 in the FA Cup Final.
But Gynn, now 56, is a world away from Wembley on his round just outside Coventry. He said: "I'm up at 4am and off to the sorting office. I really enjoy being a postie.
"I have worked for the Royal Mail since quitting football. I still keep my hand in at football by working for Opta at Coventry providing all their stats."
The switch from pitch to postie came when Gynn was forced to retire in 1995 due to injury while at Stoke City.
He lived off his football earnings for nearly a year but with a new delivery coming in the form of his son, Gynn knew he needed something else.
Bizarrely he knew of other players around the country who had gone down the postman route so he chanced his arm and applied in Coventry.
Speaking to FourFourTwo, he said: “At the interview they said that they were looking for someone who could work well in a team, so obviously my playing days stood me in good stead.
“When I first started I’d get people saying ‘Aren’t you Micky Gynn, the footballer, why are you delivering letters?’
“I also got called Postman Pat, although I’ve never had a black and white cat called Jess. We had a tabby cat called Jazz who followed me on my round for a few years, but he died last year. He’d have probably jumped in my van if I’d had one.”
A new job meant a new schedule to stick to. Up at 3am, home for 5am – time for breakfast, a quick shower and a check of the sports headlines – before going back out on rounds until about 3pm.
Then it’s bed for 8.30pm ahead of another early star the next day.
A nippy midfielder, Gynn made a name for himself for Coventry in the middle of the park. And he’s needed all those evasive skills as a postman too it seems, with the traditional dogs chasing after him.
But there was no avoiding a car one time as it came round the corner and he was sent flying off his bike. They gave him an electric car after that although he still prefers to do his rounds on foot if he can.
From delivering car bumpers to insects, Gynn has seen it all in his time – and heard it all too with plenty of village rumours flying around, although he’s keeping his lips sealed on those.
As well as delivering his own post, Gynn also worked in the area covering Coventry’s City’s training ground.
He told BirminghanLive: “The car park was a bit different to when I used to use it.
“I didn’t see many Peugeots in there, it was all these flash cars, sports cars – everything. “The players were training as I was driving past the pitch and I was wishing I was out there.”
He did get back out on the pitch in 2005 for his testimonial match at Highfield Road, the penultimate game played there before its demolition.
Gynn spent ten years at the Sky Blues following his £60,000 switch from hometown club Peterborough United in 1983.
His red letter day arrived in 1987 as one of the midfield generals behind Coventry’s FA Cup win beneath the old twin towers.
Although Gynn's departure from the club six years later came in start contrast.
Gynn told FourFourTwo: “I’ll never forget the day Coventry City let me go – or the manner in which they ended my time at the club. It was a two-minute meeting with manager Bobby Gould in 1993.
“I’d been there for 10 years and was part of the 1987 FA Cup final team, I thought I deserved more than two minutes. I don’t know where Bobby Gould is these days, but I know where I’d like him to be.”
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