Brentford Westbrooke began his career in the
academy at
Chelsea, before moving to
West London neighbours Brentford in 2011 and signing scholarship forms at the end of the
2012–13 season. By the completion of his scholarship in April 2015, he had made 55 appearances and scored four goals for the
youth team, in addition to scoring two goals in eight matches for the
Development Squad during the
2014–15 season. Westbrooke signed a one-year Development Squad contract for the
2015–16 season and by November 2015 he had impressed sufficiently to sign a one-year extension. He finished the 2015–16 season with 23 appearances and one goal. Westbrooke was named
captain of the new
B team for the 2016–17 season and signed a new one-year contract on 17 February 2017. He topped the B team's appearance-chart during the 2016–17 season, making 38 appearances and scoring six goals. He also voted the B Team Players' Player of the Year. Westbrooke was called into the first team squad for the final two matches of the
2016–17 season and made his debut in the West London derby with
Fulham as a 76th-minute substitute for
Konstantin Kerschbaumer on 29 April 2017. for both of whom he appeared sparingly. He departed
Griffin Park on 7 May 2018.
Coventry City On 7 May 2018, Westbrooke joined
Coventry City on a two-year contract on a
free transfer, with the option of a further year, effective 1 July 2018. The club's victory in the
2018 League Two play-off final, after the announcement of his transfer, meant that he began his time with the club in
League One. After a substitute appearance in an
EFL Trophy group stage match, Westbrooke made his full debut for the club with a start in a 1–0 win over
Southend United on 29 December 2018. Westbrooke broke into the team and made 33 appearances and scored four goals during the
truncated 2019–20 season, which ended with promotion to the
Championship as League One champions. After making 41 appearances and scoring four goals during his two seasons with Coventry City, Westbrooke transferred out of the club in August 2020. He made 49 appearances and scored three goals during a
2020–21 season which culminated in relegation to
League Two. After appearing in the first two matches of the
2021–22 season, A move did not materialise before the end of the summer
transfer window and Westbrooke remained at the
Memorial Stadium. He made a further seven appearances, predominantly in cup competitions, Westbrooke made 12 appearances during his spell and in his absence, Though he started in the opening match of the regular season versus
Forest Green Rovers, A move did not materialise before the end of the summer transfer window. After making just two EFL Trophy appearances since the opening day of the season, He made 61 appearances and scored four goals during years at the Memorial Stadium. Westbrooke joined League Two club
Doncaster Rovers as a
free agent on 24 March 2023 and signed a contract running until the end of the
2022–23 season. He made eight appearances and signed a one-year contract at the end of the season. Either side of three months out with a thigh muscle tear suffered in early December 2023, Westbrooke made 34 appearances and scored two goals during the
2023–24 season, He signed a new two-year contract in March 2024, effective 1 July 2024. Further thigh problems restricted Westbrooke's appearances during the first half of the
2024–25 season. He regained his fitness in March 2025 and ended the 2024–25 League Two championship-winning season with 10 appearances. On 1 October 2025, having failed to make an appearance to date during the
2025–26 season, Westbrooke joined National League club
Scunthorpe United on a loan that was later extended until the end of the season. He was released by Doncaster Rovers at the end of the 2025–26 season. == Personal life ==