Kensdale joined Colchester United's Development Centre at the age of seven and progressed to the club's Academy two years later.
He rejoined the club on loan in March 2018 and then early in the 2018–19 season prior to making his first-team debut for Colchester in November 2018.
[5][6] Kensdale joined Isthmian League North Division side Maldon & Tiptree for his first experience of men's football.
[11] On 13 November, Kensdale made his first-team debut in Colchester's EFL Trophy game against Cambridge United.
[13] After becoming the first Colchester United player born after 2000, Kensdale signed his first professional contract on 24 December 2018, committing until summer 2021.
[14] On 11 October 2019, Kensdale joined National League South side Bath City in a month-long loan deal.