Fitzroy Simpson is a distinguished former professional footballer whose career spanned two decades, showcasing his versatility as both a midfielder and left back. He began his professional journey with Swindon Town, where he joined the youth team in 1987 and quickly made an impact by signing a professional contract the following year. His debut match, although marked by a red card, set the stage for a career filled with determination and resilience. In 1992, he made a significant move to Manchester City for £500,000, where he honed his skills in the Premier League, contributing to the team’s competitive spirit during his tenure.

After his time at Manchester City, Simpson transitioned to Heart of Midlothian, where he faced challenges but ultimately found success at Walsall under the guidance of Ray Graydon. His contributions were pivotal in helping Walsall reach the Football League Second Division play-off final, showcasing his ability to perform under pressure. Although he missed the final due to injury, his efforts throughout the season were instrumental in the club’s achievements.

Simpson’s career also included stints in the Irish Premier League with Linfield and non-league football with Telford United, Havant & Waterlooville, and Eastleigh. His return to football with Havant & Waterlooville demonstrated his passion for the game, and he continued to make valuable contributions until his retirement.

On the international stage, Simpson proudly represented Jamaica, earning 43 caps and scoring three goals. His participation in the 1998 FIFA World Cup, where he played in all three group stage matches, highlighted his status as a key player for the ‘Reggae Boyz.’ Simpson’s leadership was further exemplified when he captained his final international match, leaving a lasting legacy in Jamaican football.