Initially starting at Middlesbrough as a defender, Gary made 156 League appearances over the course of five seasons, and helped secure them a promotion to the Football League Second Division in 1987, and First Division in 1988. Whilst at the club Gary was regarded as one of the most influential defenders in England, despite relegation he still played for them in the Second Division. In 1989, Gary moved to Manchester United for a fee of £2.3 million.
Upon moving to Manchester United, Gary’s transfer fee broke the national record for a defender, on top of being the highest fee between clubs in Britain, and the second-highest fee to be paid by a British club - only just second to Ian Rush's return to Liverpool from Juventus a year prior.
Renowned mostly for his defensive prowess, forming one-half of the best central defensive partnerships in the club's history with Steve Bruce, Gary scored a memorable goal in the 1992–93 season, straight into the bottom corner from the edge of the penalty area. By the end of the 1996 season, Manchester had won their fourth league title in five seasons.
Whilst playing for Manchester United, Gary was credited for the FA Cup in 1990, 1994 and 1996, the UEFA Cup Winners' Cup in 1991, the Football League Cup in 1992 and Premier League titles in 1993, 1994, 1996 and 1997. Prior to retiring in 2001, and moving to feature as a TV sports pundit, Gary returned to Middlesborough for 55 league appearances between 1998 and 2001. At present, Gary regularly features as a public speaker at conferences, functions and Q&A workshops up and down the country. Audiences revel in his stories from football’s glory years, as the experienced and eloquent speaker shares anecdotes from his footballing career.