Terry Phelan established a significant career as a professional footballer, notably contributing to Wimbledon’s historic victory in the 1988 FA Cup Final against Liverpool. After making his senior debut for Leeds United during the 1985–86 season, he moved to Swansea City in 1986 before joining Wimbledon in 1987, where he was a key player in their celebrated upset win. Phelan’s impressive performances led to a £2.5 million transfer to Manchester City in 1992, a fee that equaled the British record for a defender and set a new club record for Manchester City at the time. He made 122 appearances for Manchester City over three and a half seasons and also represented the Republic of Ireland national team 42 times between 1991 and 2000, including at the 1994 FIFA World Cup.

Currently, Phelan serves as the Technical Director of South United FC in the Indian I-League 2nd Division, a position he took up in 2019. In addition to his leadership role in football development, he is a prominent football pundit for Sony Sports Network and Sports18, providing expert analysis and insights to global audiences. His career exemplifies a comprehensive engagement with football, spanning professional play at the highest level, tactical coaching, and insightful media commentary, making him a highly respected figure in the sport.