Wide midfielder Ollie came through the academy at Forest Green Rovers before representing Cirencester Town and Frome Town. He spent the next five seasons with Metropolitan Police; twice helping them into the play-offs – including chipping in with 14 assists in 31 appearances during the 2021-22 campaign – before joining Enfield in the 2023 off-season, contributing a further 14 assists and 6 goals to help the Towners to promotion.