A youth product of Stevenage Blue Socks, he joined the academy of West Ham United at under-8 level.[4] He started playing with their U23 development team in 2018 as a 15 year old, signing his first professional contract with the club on 16 June 2021.[5] He made his professional debut with West Ham on 21 October 2021, coming on as a late substitute in a 3–0 UEFA Europa League group stage win over Genk.[6]
On 26 August 2022, Chesters joined Colchester United on-loan for the remainder of the 2022-23 season.[7]
In January 2023, Chesters was recalled by West Ham having made 18 league and cup appearances for Colchester.[8]
In February 2024, Chesters joined Salford City on loan for the remainder of the 2023–24 season.[9]
On 24 May 2024, West Ham announced that Chesters would be released at the end of the 2023–24 season.[10]
Salford City
On 5 June 2024, Chesters agreed to return League Two side Salford City on a permanent basis, signing a two-year deal.[11]
Style of play
Chesters is described as a "livewire attacking midfielder capable of opening up the tightest of defences".[12]
Career statistics
As of match played 17 March 2024
Appearances and goals by club, season and competition