*Club domestic league appearances and goals, correct as of 18:25, 31 October 2024 (UTC) ‡ National team caps and goals, correct as of 20:35, 13 October 2020 (UTC)
Whittaker began his playing career at Derby County's academy before making his senior debut for the club in August 2019.
Club career
Derby County
On 12 August 2019, Whittaker made his professional debut as an 87th-minute substitute in the EFL Cup for Derby County against Scunthorpe United[3] and made his first start in a 3–0 defeat away to Nottingham Forest in the same competition. He signed a new contract with Derby running until June 2023 on 22 January 2020.[4] Whittaker finished the season with three starts and eighteen substitute appearances and scored his first career goal with the second Derby goal in a 3–1 win away to Birmingham City on the final day.
Whittaker started the 2020–21 season by scoring the winning-penalty in a 3–2 shootout victory over Barrow in the EFL Cup and continued making frequent substitute appearances throughout the course of the season.
Swansea City
On 1 February 2021, Whittaker joined fellow Championship side Swansea City on a four-and-a-half-year deal.[5] Nine days later, Whittaker scored on his debut for the Swans in a 1–3 home defeat by Premier League side Manchester City in the FA Cup.[6] His first league goal came on 1 May 2021 in the penultimate game of the season to equalise in an eventual 2–1 victory over Derby County that kept his former side firmly in the relegation battle.[7]
On 1 January 2022, Whittaker joined Lincoln City on loan for the remainder of the season.[9] He made his debut against Oxford United on 8 January 2022, starting and scoring in the game.[10]
Plymouth Argyle (loan)
On 20 July 2022, Whittaker joined Plymouth Argyle on a season-long loan deal.[11] Having scored three vital goals and claiming an assist across September 2022, Whittaker was awarded the EFL League One Player of the Month Award with Argyle sitting top of the league.[12]
On 4 January 2023 Swansea City exercised their recall clause in his season-long loan. Whittaker had scored nine goals and created seven assists in 25 third-tier appearances since moving to Home Park in July 2022.[13]
Return to Plymouth Argyle
On 17 July 2023, Whittaker returned to Plymouth Argyle in a deal reported to be worth around £1 million plus add-ons – a record fee for the club.[14]
Whittaker, alongside new record equalling signing Bali Mumba, would go on to score on his debut in a 3–1 win over Huddersfield Town at the time managed by former Plymouth Argyle manager Neil Warnock.
On 23 September 2023, Whittaker scored a hat-trick for Argyle in a 6–2 win against Norwich City.[15]