A 4–1 win over Yu Delu qualified O'Sullivan for the 2016 Riga Masters and he beat Luca Brecel 4–0, before being unable to pick up a frame himself in the second round against David Gilbert. After losing eight of his next nine matches he knocked out Robbie Williams, Mark King and Mitchell Mann at the Scottish Open all by 4–1 scorelines to reach the last 16 of a ranking event for the first time. O'Sullivan led Yu 3–2, but lost 4–3. O'Sullivan entered Q School at the end of the season in order to attempt to remain on the tour. He lost 4–0 to Allan Taylor in the final round of the first event and 4–3 to Paul Davison in the fourth round of the second, but had done enough to earn a new tour card through the Q School Order of Merit.