At the World Open, Woollaston recorded 5–2 and 5–1 wins over Gary Wilson and Ding Junhui, and made a 135 to level his third round tie with Joe Perry at 4–4, but lost the deciding frame. He got to the fourth round of the English Open by beating Cao Yupeng 4–1, Zhang Anda 4–3, and Ali Carter 4–2, and was defeated 4–3 by Liang Wenbo. Woollaston overcame Elliot Slessor 6–5 and Paul Davison 6–4 at the UK Championship, before losing 6–2 to John Higgins. He recorded his first win over Neil Robertson by edging him out 5–4 in the first round of the German Masters and was then knocked out 5–2 by Barry Hawkins. Woollaston also played in the second round of the China Open, but lost 5–4 to Hossein Vafaei. His final-round qualifier match for the World Championship with Zhou Yuelong went to a deciding frame, which Woollaston lost.