But beyond the Crazy Gang and Cup glory, Phelan enjoyed a successful playing career, turning out for major clubs Chelsea, Manchester City and Leeds United.
Now working in India, where he was been involved in local football for over 10 years, Phelan spoke with Tribalfootball.com about his career and his ambitions - which include his hopes with South United in India.
Terry, the first question is the most obvious - what is it like being part of such famous FA Cup folklore?
"First and foremost, I would say that winning an important cup like the FA Cup, with all its history in British football, is always a great achievement. We played at the old Wembley, an iconic stadium. Everyone was saying we were going to lose to a big team like Liverpool, but for all of us at Wimbledon, it was more about enjoying the moment and giving our best.
"For me, as a young boy, it was a dream come true because I remember watching the FA Cup as a kid, dreaming of playing in the final one day. Before the game, of course, we were excited and felt the pressure, but as it started to flow, we grew more confident. Our talented players began to play with more belief. I think we had great courage to perform like that against Liverpool, and in the end, we made history."
After Wimbledon, you transferred to Manchester City for a British record transfer fee for a defender at the time, which was also a club record. How did you find things at City?
"To be honest with you, I could have gone to places like Ajax, Barcelona, Celtic, Manchester United, Tottenham Hotspur, Rangers, and Everton. I had many offers, but in the end, I chose City for what was a record transfer fee at the time.
"Even back then, City was a fantastic, massive club, and I had a great time there. I always tried to give my 100% whenever I played. I enjoyed my time at City because I fulfilled my dream of playing for my city's club. I spent three wonderful years there, although there were a lot of changes during my time—managers and ownership shifts."
The City of today must seem like a world away from the time you played there...?
"Listen, the world has evolved, buildings have evolved, and it's natural that the club has evolved too. Back then, City paid £2.5 million for me, which was a record fee, but now you see players coming in for millions and millions of pounds. It's a business now—you have more TV rights, sponsorships, and it's all completely different from back then. But despite all the changes, one thing has stayed the same: under the green grass, it's still football, and at the end of the day, that's what matters."
Is today's City under Pep Guardiola the greatest team we've seen? Is this is the greatest era in English football?
"You have to give credit to (Roberto) Mancini and (Manuel) Pellegrini first because they helped raise City to the level it’s at today. Both won the Premier League and cups, pushing the club forward. Of course, when Pep came in, he got the players he wanted and brought his style of football, taking the team to an even higher level.
"He bought the right players with the right mentality, thanks to the club's support, and Guardiola has been very successful. To say if this is the greatest team ever in English football, you’d need to compare it with teams like Manchester United, Chelsea, and Liverpool during their golden eras. City is one of the greatest teams now, but they still have work to do to be considered the greatest in English football history."
You played at Chelsea in an exciting time, with Ruud Gullit then in charge...
"Yes, during my time at Chelsea, I had the chance to play with many great players from whom I learned a lot, including Ruud. He was a phenomenal player, and it was a pleasure to play with him. As for being coached by him, some people say he wasn’t ready to be a coach back then, while others say he was. But in the end, he won trophies, and that’s what matters. When you’re at a big club like Chelsea, the important thing is winning trophies."
Who were the best players you played with - and you're toughest opponents?
"Look, I played with (Gianfranco) Zola, (Gianluca) Vialli, and Mark Hughes. I also had the chance to play with great players in the national team, like Roy Keane. When I look back, I feel lucky to have shared the dressing room with these phenomenal players.
"As for the players I’ve faced, internationally, I played against players like (Roberto) Donadoni and (Roberto) Baggio. At the club level, there were many, like (Ryan) Giggs. But the toughest opponents were Alan Shearer, Ian Wright, Robbie Fowler, and I could go on and name many others."
Now you're working in India - how have you found that?
"Towards the end of my career in England, I didn’t want to become a journeyman, so after Fulham, I went to America. I won some trophies there and started coaching. Then I got an opportunity to go to New Zealand as a player and head coach.
"I thought, ‘Why not?’ and spent six wonderful years there. I enjoyed it and felt the need to give back to football. In 2010, I got an offer to go to India, and I said yes because I’m not afraid of challenges. It wasn’t easy, but I stayed for two years before returning to England to work in the academy system.
"In 2014/15, I came back to India to work with Kerala Blasters, where I spent five great years. Then I moved to Bangalore in 2019 to work with South United as a technical director, and now I’m the sporting director. It’s been a great journey, not just with clubs but also with media here, working as a pundit covering European tournaments and leagues.
"I feel part of the culture now, and the people have been brilliant. The league has improved a lot, but we still have work to do to take Indian football to the next level."
So what's next for Terry Phelan? Remaining in Asian football or returning to Europe?
"In football, you never know what’s around the corner. It could be India, it could be Europe — it depends on what opportunities come up because, to be honest, I’m not actively looking. If a good project comes up, I’m open to it, but for now, I’m happy at South United and excited to see where this project will take us in the next few years.
"The football industry is unpredictable — one minute you’re in, the next you’re out. But I don’t think too far ahead; I just enjoy every day of my work. I’m proud to still be part of the game, and I hope to stay involved until I’m 96 years old."