He made his senior debut on 30 August 2016, in a 2–1 defeat to Luton Town in an EFL Trophy match at Priestfield Stadium.[4] Dickenson made his English Football League debut away at Bury on 4 March 2017, coming on as a first half substitute for the injured Ryan Jackson. On 20 May 2017, Gillingham announced that Dickenson had been released at the end of his contract.[5]