Hendry started the 2008–09 season with two losses in his first matches. He was beaten 1–5 by Stephen Lee in the Northern Ireland Trophy and 4–5 by Ricky Walden in the Shanghai Masters. He had more success in the Grand Prix, however, winning his first-round match with David Gilbert 5–4, before succumbing to the eventual winner, John Higgins, 2–5 in the next round. However, in the next ranking event, the Bahrain Championship, he reached the semi-final, but he lost 4–6 to Matthew Stevens. In the next three professional tournaments, the 2008 UK Championship, the Masters and the Welsh Open, Hendry lost in the first round to Stephen Lee, Neil Robertson and Martin Gould respectively. He found some form in the China Open, beating Robert Milkins and Ricky Walden, but lost his quarter-final match to Peter Ebdon, the eventual winner of the tournament.