Ollie was in the under-16 squad at Exeter City's Centre of Excellence in 2009/10 during which time he played in the FA Youth Cup against Cheltenham in October 2009. He then progressed to become a City trainee between 2010 and 2012 before being offered a professional deal in 2012.

Released early after spending time on loan at Barnstaple Town, Ollie moved on to Bath City followed by a spell at Weston-super-Mare during 2013/14. Switching clubs several times over the next two seasons, he was at Paulton Rovers, Evesham Town and Frome Town whilst persuing his studies at Hartpury College in Gloucestershire. Eventually settling with Truro City he subsequently appeared fpr Tiverton Town before rejoinng Frome at the start of 2018.

Remaining with the Somerset club for a season-and-a-half,  Ollie signed for Salisbury in the summer of 2019 and spent three seasons in Wiltshire before signing once again for Truro City at the start of 2022/23.

Now having played nearly three hundred games at National League and Southern League level he left Truro after the club's promotion to National League South in May 2023 and opted to play closer to home with Topsham Town before joining Exmouth Town in June 2024.