Started his career at Marlow United, before moving to Reading where he progressed through the Academy system.

Represented England at Under 15 and Under 16 level, contributing with a goal in a win against the USA.

Olly signed his professional contract with The Royals at the age of 17 and went on to make his First Team debut in a defeat at Luton Town. At the end of this campaign he made the switch to Wycombe Wanderers, scoring twice on his second start.

Moved to Farnborough in September 2022, making his debut in an away victory at Cheshunt.

Returned to Boro also in September 2023, following stints with Aldershot Town and Ayr United.