Woollaston qualified for five ranking events during the 2013–14 season, by far the most he has reached in a single season during his career. At the Wuxi Classic he beat Chen Zhe and Joel Walker both 5–2, before he lost 5–2 to Cao Yupeng in the last 16.&lt;ref name="2013/14"&gt;&lt;/ref&gt; Woollaston was defeated in the first round of the Australian Goldfields Open, the International Championship and the German Masters. He saw off Vinnie Calabrese and Alfie Burden with the loss of just one frame to reach the last 32 of the Welsh Open, where he came close to knocking out Ding Junhui but lost 4–3. In the minor-ranking European Tour event the Ruhr Open, Woollaston edged out reigning world champion Ronnie O'Sullivan 4–3 and then whitewashed Burden and Chris Norbury 4–0, before losing in a final frame decider to Stephen Maguire in the quarter-finals. He went a step further at the Antwerp Open by beating Joel Walker in the quarters, but O'Sullivan this time got the better of Woollaston to win 4–2 in the semi-finals. These results aided him to a 20th placing on the Order of Merit to qualify for the Finals for the third year in a row. Woollaston beat Ding, a four-time winner on the tour this season, 4–3 having been 3–0 behind to advance to the last 16 of a ranking event for the second time this campaign, where he was eliminated 4–2 by John Higgins.