City defeated Gillingham on penalties to earn a spot in the First Division before securing promotion to the Premier League the following season.
At that point, Bernstein was in discussions about the City of Manchester Stadium, which was being built to host the 2002 Commonwealth Games, becoming our future home.
It was a move that came to fruition for the start of the 2003/04 campaign and the ground has seen so many iconic moments in the years that have followed.
But the former chairman stresses that if the Gills had triumphed over City that rainy May day, things could have turned out very different.
“I think that game was the most important in our history, without any question,” Bernstein said.
“It was more than a game because it happened at a crucial moment in our history when the club had declined over many, many years and been through an intensely difficult period.
“Our stadium at the time, Maine Road, was described as the Theatre of Comedy. One can, unfortunately, understand why.
“There was so much hanging on this game. One of the main things was the potential new stadium, now called the Etihad but then the City of Manchester Stadium.
“We were in deep discussions with Manchester City Council and Sport England about the future of it but it needed the credibility of our getting a promotion out of the third tier of English football.
“Had we lost that match against Gillingham there was quite a good chance that the new stadium deal would never have gone through.
“And if that had happened, our club’s history would be a lot different.
“Manchester City Council and Sport England needed to believe that the big club that Manchester City were was going to resurrect itself and was going to get back to the big time sooner or later.
“If we couldn’t get out of the third tier of English football, that credibility would undoubtedly have been affected.
“Would that mean the deal wouldn’t have happened? I really don’t know. But I think there’s a good chance they would have said ‘we are keen to support you but frankly you’re still at the third level, it’s too big a jump, we can’t take the risk’ and the whole thing would not have happened.
“If that had played out, then City would have become a much less interesting investment.
“I thought it was such a seminal moment for the club – a real watershed moment.
“It’s so fascinating to think that this one match could have such a ripple effect on the club.”
Bernstein’s position as a central character in Manchester City’s history is the subject of his wonderful new book.
Called ‘We Were Really There’, the second part of the title reads ‘The Rebirth of Manchester City’ and it’s a phrase that perfectly sums up this iconic moment in the story of our great club.
“I used the term rebirth in the book title and I believe that game is when the rebirth of our great club began, without any question,” he continued.
“You had the feeling afterwards that maybe fate was on our side at last. Something huge had happened.
“Fans had left the stadium and then come back in when we were getting back into the game.
“To come through that, I felt we could really start using the momentum. That’s a very good word in life and in sport – momentum. The belief in ourselves returned.
“And then look what happened the following season – another promotion.”
That’s not all that’s happened since.
In the 25 years following the Play-Off Final, City have won a remarkable 24 major trophies.
We’ve seen so many great players and cheered on our Centurions, Fourmidables, Treble Winners, Champions of the World and History Makers.
Bernstein has been a key observer in those years although he admits he could never have foreseen our levels of unprecedented success.
“When I was chairman down in the third level of football, I said my ambition was that Manchester would become the Milan of English football with two great sides.
“My dream was to get up close to the then dominant Manchester United.
“But to see City achieve this incredible level of success has been amazing.
“In my view, we must be regarded as the greatest team ever in the history of English football now that we have won four-in-a-row on top of the Treble success. No-one can argue with that!
“If you’d have told me about that 25 years ago, I would have said ‘no, no that’s a dream too far’.
“It’s the greatest recovery story in the history of English sport.
“And without the foundations we put in place in 1999, this couldn’t have happened.”
But why write a book?
Bernstein says he was keen to chronicle his pride at being chairman of Manchester City, a club he has supported passionately all his life.
“I wanted something to leave behind – a personal record of a lifetime highlight” added Bernstein.
“People of a certain generation think that success started when our present owners bought the club.
“Of course, the job they have done has been incredible. The owners and those running the club deserve great credit. I am immensely proud of where the club is now, as I’m sure my fellow fans are.
“But I believe the success started when we built the foundations of the club and got the club back into shape.
“I wanted to have that on record for fans in the future to understand that the club was in a really difficult position.
“I had a great set of people to work with – Alastair Macintosh, Chris Bird, Dennis Tueart and Bernard Halford were all fantastic.
“Over the course of two, three or four years, on more than one occasion during a board meeting I said to my colleagues: ‘Guys, we should be proud of ourselves, we really have got our act together, we have made tough decisions, we haven’t compromised, we have the fans on-side, we are disciplined, this is being run like a football club should’ and with the fans as they always should be front and centre.
“Manchester City Football Club - that word club means something. I am extremely proud of that and wanted to give a feel for what it was like being in the trenches through a very difficult period.”
David Bernstein’s book ‘We Were Really There: The Rebirth of Manchester City’, written with football journalist and author Tim Rich, is available to buy now.
