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.^[3][4][5] By the completion of his scholarship in April 2015, he had made 55 appearances and scored four goals for the youth team,^[6][7][8] in addition to scoring two goals in eight matches for the Development Squad during the 2014–15 season.^[9] 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.^[10][11] He finished the 2015–16 season with 23 appearances and one goal.^[12]

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.^[4] He topped the B team's appearance-chart during the 2016–17 season, making 38 appearances and scoring six goals.^[13] He also voted the B Team Players' Player of the Year.^[14] 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.^[2]

Mounting injuries led to Westbrooke's inclusion on the first team bench for a league match versus Ipswich Town on 19 August 2017, but he remained an unused substitute during the 2–0 defeat.^[2] Westbrooke subsequently spent much of the first half of the 2017–18 season away on loan at National League clubs Solihull Moors and Leyton Orient,^[15][16] for both of whom he appeared sparingly.^[13][17][2] After his return on 10 January 2018,^[13][17] Westbrooke spent the remainder of the 2017–18 season with the B team.^[18] He departed Griffin Park on 7 May 2018.^[19]

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.^[20] 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.^[21] 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.^[22] He had a short run in the team in late-January and early-February 2019 and finished the 2018–19 season with eight appearances.^[22][23]

Westbrooke broke into the team and made 33 appearances and scored four goals during the truncated 2019–20 season,^[24] which ended with promotion to the Championship as League One champions.^[25] After making 41 appearances and scoring four goals during his two seasons with Coventry City,^[26] Westbrooke transferred out of the club in August 2020.^[27]

Bristol Rovers

On 3 August 2020, Westbrooke signed a three-year contract with League One club Bristol Rovers for an undisclosed fee.^[27] He made 49 appearances and scored three goals during a 2020–21 season which culminated in relegation to League Two.^[28][29] After appearing in the first two matches of the 2021–22 season,^[30] manager Joey Barton dropped Westbrooke from the matchday squad and revealed that he was free to leave the club.^[31] A move did not materialise before the end of the summer transfer window and Westbrooke remained at the Memorial Stadium.^[32] He made a further seven appearances, predominantly in cup competitions,^[30] before joining League Two club Stevenage on loan until the end of the 2021–22 season on 17 January 2022.^[33] Westbrooke made 12 appearances during his spell and in his absence,^[30] Bristol Rovers were automatically promoted back to League One.^[29]

Returning to the Memorial Stadium for the 2022–23 pre-season, manager Joey Barton stated that Westbrooke's performances in training and matches had "done nothing but enhance his claim" for a first team place.^[34] Though he started in the opening match of the regular season versus Forest Green Rovers,^[35] Westbrooke was subsequently barred from first team training and was told he was free to leave the club.^[36] A move did not materialise before the end of the summer transfer window.^[37] After making just two EFL Trophy appearances since the opening day of the season,^[35] Westbrooke's contract was terminated by mutual consent on 23 January 2023.^[38] He made 61 appearances and scored four goals during 2+1⁄2 years at the Memorial Stadium.^[26]

Doncaster Rovers

Following a period training with Walsall,^[39] 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.^[40] He made eight appearances and signed a one-year contract at the end of the season.^[35][41] Westbrooke made 24 appearances and scored two goals during the first half of the 2023–24 season,^[42] before missing three months after undergoing surgery on a thigh muscle tear in early December 2023.^[43][44] On 28 March 2024, he signed a new two-year contract.^[45]