Born in Leicester, England, Woollaston began his professional career by playing the Challenge Tour in 2003, at the time the second-level professional tour. He first entered the Main Tour for the 2004–05 season, but was unable to retain his place for the following season. He regained his place for 2006–07 by winning the European Under-19 Championship. He was awarded a concessionary place for the 2007–08 tour. Woollaston has twice reached the final group stages of the Grand Prix in 2006 and 2007, enjoying a marginally better tournament in 2006 by winning two matches compared to none in 2007. He also reached the final stages of the 2007 Welsh Open, beating David Gray to reach the second round, in which he lost 2–5 to seven-time World Champion Stephen Hendry.