 Despite signing a contract with Cambridge in January 2008 keeping him at the club until 2010, Wolleaston signed for Conference rivals Rushden & Diamonds for an undisclosed fee on 2 June 2008, with Cambridge manager insisting finances would be tight following a series of departures.Wolleaston had played 92 league games for Cambridge, scoring nine goals.Wolleaston made his debut for Rushden in a 1–0 victory against newly promoted Eastbourne Borough on the opening day of the 2008–09 season.