 Wolleaston started his career with Chelsea, but he only made two first-team appearances in five years, and instead had short loan spells with Bristol Rovers, Nottingham Forest, Portsmouth and Northampton Town.Following his release from Chelsea, he moved to Bradford City, but was released after one season, in which the club suffered relegation and administration.He spent more than a season with Oxford United but left following a series of injuries and instead dropped into non-league with Cambridge United, for whom he played 92 league games in three seasons, until he moved to Rushden & Diamonds in 2008.