As a player, he was a winger who notably played in the Premier League for Queens Park Rangers, West Ham United and Manchester City.
He won the 1997 Match of the Day Goal of the Season after scoring a bicycle kick in an FA Cup tie against Barnsley.
Following his retirement, Sinclair largely worked as a pundit on both television and radio, most notably for BBC Sport on Football Focus and Final Score.
Sinclair was inducted into the Hall of Fame at Bloomfield Road when it was officially opened by former Blackpool player Jimmy Armfield in April 2006.
In total Sinclair spent five years at Upton Park, playing in a variety of positions including wingback,[9] left and right wing and as a striker when called upon.
[11] At the beginning of his career at Manchester City, he played on the left wing, where he had performed for England at the 2002 FIFA World Cup.
[13] He began the season as a first-team player, scoring his first Cardiff goal on 24 September in a 4–2 win in the League Cup over West Bromwich Albion.
[18] On 21 February 2018, he joined North West Counties Football Premier League club Squires Gate at the age of 44 after a 2014–15 season at Lancaster City.
[19] In 1994, Sinclair was called up to the Republic of Ireland squad by Jack Charlton, but was unable to declare for his mother's homeland as he had already played at U21 level for England.
[citation needed] As of October 2021, Sinclair runs a football academy with Bamber Bridge manager Jamie Milligan.
[24] Following his retirement, Sinclair largely worked as a pundit on both television and radio, most notably for BBC Sport on Football Focus and Final Score.
[29] In January 1999, Sinclair was convicted of causing criminal damage to a car, following a night of drinking with other West Ham players at the club's Christmas party in Romford.
[30] In November 2017, Sinclair was arrested on suspicion of drink driving, common assault and criminal damage after a woman was hit by a car in Lytham St Annes.
[32] He was sentenced to 150 hours of unpaid work, disqualified from driving for 20 months and ordered to pay £500 compensation to the abused police officer.