Woollaston lost 4–1 in the semi-finals of the Riga Open to Tom Ford and reached the quarter-finals of the Haining Open, but was beaten 4–2 by Robert Milkins. Two deciding frame victories over Robbie Williams and Yu Delu saw him reach the third round of the International Championship.&lt;ref name="2015/16"&gt;&lt;/ref&gt; After recovering from 5–2 down to Joe Perry, he almost won 6–5 for the third time in the week but this time lost the decider. Woollaston was beaten 6–2 in third round of the UK Championship by Shaun Murphy. He reached the quarter-finals of the Welsh Open for the second year in a row, but was defeated 5–1 by Joe Perry. Another came at the PTC Finals with wins over Jimmy Robertson and Matthew Selt and, though he had multiple chances to win the last frame, he lost 4–3 to Murphy. Woollaston lost 10–9 to Chris Wakelin in the first round of World Championship qualifying. He recorded a new career-high end of season world ranking of 27.