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Born in Hillingdon, Middlesex, Ray started his career with Senrab in Wanstead Flats. He went on to make his name in the 1970s with boyhood club Chelsea after joining as an apprentice. Ray made his debut against Norwich City at the age of 17, coming on a substitute in a 3-0 home league win.

Wilkins established himself as a fixture in the side the following year, although he was unable to save Chelsea from from relegation that season. In 1975, at the age of 18 Ray was handed the captaincy of Chelsea by new manager Eddie McCreadie. He emerged as one of Chelsea’s key players of that period, leading them to promotion in the 1976-77 season.

In the 1978-79 season Ray headed north to join Manchester United for a fee of £800,000. At United Ray went of to win the FA Cup in 1983, getting himself on the scoresheet in the process. A year later, United accepted an offer of £1.5 million from Italian giants Milan. Wilkins and his family settled quickly in Italy and Milan reached the final of the Coppa Italia in 1985.

Ray left A.C. Milan in 1987 in join French side Paris Saint-Germain where he stayed for only four months before moving to Glasgow Rangers for a fee of £250,000. During his time with Rangers he won the Scottish League title in 1989 and the Scottish League Cup. He also scored a memorable goal in an Old Film derby against Celtic.

Wilkins then moved on to join Queens Park Rangers after a decade away from home. He spent four years with QPR before moving on to become player-manager after Gerry Francis left in November 1994. In his first season in charge QPR finished 8th in the Premier League and reached the FA Cup quarter finals. Wilkins left QPR at the start of the 1996-97 season after the club was bought by media tycoon Chris Wright.

Ray was called up to play for England for the first time in 1976 and quickly made his Debut against Italy. He was to become a permanent fixture in the England squad for a decade to come. He achieved one of his career highs after helping England quality for the 1980 European Championships. Which was the first tournament England had reached for a decade. Wilkins made 84 Caps for England scoring 3 goals and was giving the captains armband on 10 occasions.

Since retiring as a player, Ray has had managerial and coaching roles with Fulham, Chelsea, Watford, Millwall and the England under 21′s. Wilkins has also appeared as a commentator for Sky Sports, particularly on their Champions league coverage.