The ultimate squad player for one of the best English club teams in living memory, even now he is not the first name that pops into your head when you think of that great treble-winning Manchester United side of 1999.
In fact he is most fondly remembered for taking centre-stage in the post-match celebrations of that famous 2-1 win over Bayern Munich, despite not playing a single minute in the Champions League that season.
But it would be unfair to boil a career that includes two Premier Leagues, two FA Cups and a Champions League down to one celebration – regardless of how iconic it is.
There’s a reason May is still fondly remembered by United fans, despite making just 69 league starts across nine years.
And there’s a reason he’s still highly regarded among Blackburn Rovers fans, after helping them win promotion to the Premier League in 1992 before keeping his place in a team that finished fourth and second in the top tier after that. So, it’s quite understandable that 18 years on from that night in Barcelona, he’s tired of talking about that celebration.
“It’s just one of those things, sometimes you get carried away with celebrations,” he said. “Obviously being the first club to win the treble and still the only club to win the treble was a very proud moment for us all.”
Born in Oldham, May was a football fanatic growing up, and went to watch Bury, Manchester City, and Oldham as a child, depending on who was at home.
“I just loved watching football,” he said. “Everybody says I was a City fan, but I was an Oldham fan as well. Only team I didn’t go to watch was United because nobody would take me. Now, 100 per cent a United fan.”
He started his career as a trainee at Blackburn, playing right-back and centre-back for the youth teams before graduating to the first team at the age of 18. Rovers were nearly relegated from Division Two in 1991, but then Kenny Dalglish arrived.
Blackburn won promotion to the newly-named Premier League in 1992 and finished fourth and second in their first two seasons with May retaining his place in the team despite Rovers splashing the cash in the transfer market.
After losing out to Manchester United in the title race, May was signed by Sir Alex Ferguson for £1.2million as a long-term replacement for Steve Bruce.
The next year, Blackburn won the title. At that stage his medal cabinet was bare, but did he have any second thoughts while he watched his former team-mates lift the trophy?
“No, I knew I’d gone to the right club,” he said. “It wouldn’t be long until United were back winning things. Fair credit to Blackburn, they were best team that year because they won the league. The year after, we won the league and the FA Cup, so not too bad.”
And it was that 1995/96 season when May started to establish himself in United folklore. He had a lengthy period in the side while Bruce struggled with a hamstring injury and scored the opening goal in their crucial final day win over Middlesbrough that clinched them the title.
“That ranks up there as one of the best moments of my career,” he said.
“Scored the first, go on and win the game 3-0 and win the league and then following Saturday have Liverpool in FA Cup final. It’s everyone’s perfect dream really. A fabulous achievement, not just by me, by the club. Born winners, every single one.”
To this day the names of that dominant United team can be instantly recalled by most football fans – and May couldn’t bring himself to single any of them out particularly.
He says their strength lay in their team ethic.
“Eric (Cantona) did unbelievable things on his own,” smiles May. “Giggsy at times, Becks, Scholesy, Keane. Everybody could bring something to the table. When you win things, it’s not just down to individuals; it’s down to the team.
“Certain players will get picked out obviously but Fergie always used to say you win together, you lose together. Nobody takes individual plaudits, it’s a team game. We had a mix of experienced players, Brucey, Pallister, Mark Hughes, Incy, Eric, Irwin, then you had the youth of Becks, Scholes, Butt, Giggsy and Nev.
“It was the perfect blend of youth and experience and if ever you needed to rely on the experience you’re looking back at players that have been there seen it done and won everything.”
If anyone was a star, it was the manager. Sir Alex Ferguson built such a strong dynasty at United that at times, the squad policed itself.
“You knew exactly where you stood,” says May. “As soon as you walked through the doors at Old Trafford you know you have to become a winner, it’s in the DNA of the club. When you’re playing under him, even the players demand. You can’t go out there and settle for a draw. You need to win every game. We had an unbelievable squad. We had goalscorers all over the pitch. There was two players for every position and the manager rotated it perfectly.”
One of those occasions was in that fabled last few days of the treble-winning season. Fergie decided to rest Jaap Stam for the Champions League final and so May started in the FA Cup final against Newcastle.
“No disrespect to Newcastle – but there was only going to be one winner,” he shrugs. “I don’t think they had any real clear-cut chances, we just dominated from start to finish.”
And that’s how it used to be. United were favourites for every game, and swatted aside the opposition with an arrogance that was terrifying, yet earned. They’ve lost their aura since Fergie retired, but May – who works for MUTV now and watches all of United’s games – reckons Jose Mourinho is slowly rebuilding it.
“I think we’re getting there,” he said. “It’s an improvement over the years under Van Gaal.
“Look at the players he’s trying to sign, (Antoine) Griezmann, (Ivan) Perisic, they’re all attacking footballers.
“(Paul) Pogba, (Henrikh) Mkythiran and Zlatan (Ibrahimovic) are all exciting players.”
United won the League Cup and the Europa League last season, and even though May has won bigger trophies himself, he says pot-hunting is addictive. “You’re judged on winning things,” he said. “At the beginning of the season it was probably the two lesser trophies you would want to win. But listen, it’s a trophy.
“I do think you’re judged on when you end up in Premier League. Defensively we are very good, we lost five games last season, the same as (champions) Chelsea. “We drew too many at Old Trafford, when we’ve absolutely annihilated teams, but just couldn’t score. This year I think we’ll be alright.”
And May, a defender himself, knows titles are built on strong defences. “Eric Bailly has been fantastic,” he said.
“Phil Jones, before he got injured, had a run which was probably the best he’s played for the club. And (Antonio) Valencia has been absolutely outstanding at right back.
“Mourinho wanted to sign him when he was at Real Madrid, he’s the best right back in the world. He’s our most consistent performer.”
May’s honours list is surprisingly similar to Valencia’s. They both have two Premier Leagues and a few domestic cups to their name. The only difference is his European medal is the big one. And United is such a global brand these days, May is still making a living from his success at the club.
After retirement he imported wine for a few years, but ‘knocked it on the head because the lad I was with was a complete p****’.
So now, he lives in Manchester and works for MUTV. “I do the television at United and the odd trip away with the club,” he said. “We went on pre-season which was 18 days away in LA so that was good.
“Just MUTV, I love doing that, I’ve got my own show on a Thursday. It’s good. Life’s good.”