Jebbison was born in Oakville, Ontario and began playing football at the ANB Futbol youth academy.[4] He lived in Canada until he was 13, in 2017 he relocated to England with his family and they settled in Derby, with Jebbison attending Derby Moor Academy in the Littleover region of Derby.[5] Jebbison joined the Sheffield United Academy in 2018 after a successful trial.[6] After passing through Sheffield United's U18 and U23 development sides, he joined Chorley on a short-term loan on 24 December 2020,[7] having played for them twice.[8] Soon after returning to Sheffield United, he made his professional debut with them in a 2–0 Premier League loss to Crystal Palace on 8 May 2021.[5][9] Jebbison scored his first goal for the club against Everton on 16 May, becoming the youngest player to score in their first start in the Premier League.[10] On 21 May, he signed his first professional contract.[11]
On 31 August 2021, Jebbison joined League OneBurton Albion on loan.[12] On 11 September he made his debut for his loan club, coming off the bench in a 1–1 draw against Gillingham.[13] A couple weeks later on 28 September, Jebbison scored his first goal for Burton in a 2–1 home win against Portsmouth in league action.[14] Jebbison was recalled by Sheffield United on 31 January 2022.[15]
AFC Bournemouth
On 10 July 2024, Jebbison signed for Premier League club AFC Bournemouth on a four-year deal; although his contract with Sheffield United had expired, Bournemouth reportedly paid a £1.5 million training fee in compensation.[16]
On 30 August 2024, Jebbison joined Championship club Watford on a season-long loan deal.[17]
International career
Jebbison was born in Canada to a Jamaican father and English mother, and moved to England in 2017.[18] He is eligible to play for all three senior teams. He debuted with the England under-18s in a friendly 2–0 win over the Wales under-18s on 29 March 2021.[19] On 18 June, Jebbison was named to Canada's 60-man provisional squad for the 2021 CONCACAF Gold Cup.[20]