Woollaston was knocked out of the 2014 Wuxi Classic in the second round 5–3 by Judd Trump, and then failed to qualify for the next two ranking events.&lt;ref name="2014/15"&gt;&lt;/ref&gt; In the opening round of the International Championship he led Ronnie O'Sullivan 2–0 and 3–1, but went on to lose 6–4. Woollaston was also beaten 6–2 by the five-time world champion in the third round of the UK Championship, and afterward described his own performance as embarrassing. A week later he achieved the first maximum break of his career at the Lisbon Open in his last 128 match against Joe Steele, but lost 4–3 against Peter Ebdon in the next round. Woollaston won group 6 of the Championship League by seeing off Ebdon 3–0 and progressed through to the semi-finals of the winners' group where he lost 3–2 to Mark Davis.