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Ollie made seven first-team outings for Devon rivals Plymouth prior to gaining further senior action at Southern League Barnstaple and Truro, before he signed for United at the start of the 2022/23 season. It was during this season that Ollie found himself have loan spells at both Chippenham Town and Taunton Town in the National League South..

The 2023/24 season saw the defender make his break into Torquay’s First Team set up, where he went on to make the most player appearances for the Club, winning himself the Ian Twitchin trophy in the process, and also scored his first goal for the club, that being the winner in a 1-0 victory away at St Albans City.