A youth product of the Colchester United Academy since U10 level, Kennedy worked his way up through the youth categories at the club after joining from Kelvedon Hatch.[5] He made his professional debut for Colchester in a 1–0 EFL Cup loss to Birmingham City on 10 August 2021.[6] He made his English Football League debut for the club on 21 August 2021, coming off the bench in Colchester's 2–1 win at Oldham Athletic.[7]