British number three Cameron Norrie was beaten by France's Gael Monfils in the second round of the Zhuhai Championships in China.
Third seed Monfils, 33, won 5-7 6-3 6-4 and will play Spain's Albert Ramos Vinolas in the quarter-finals.
Australian sixth seed Nick Kyrgios lost his first-round match to world 74 Andreas Seppi 7-6 (7-5) 6-1.
Britain's three-time Grand Slam champion Andy Murray faces Australian Alex de Minaur on Thursday.
Former world number one Murray recorded his first singles victory at Tour level since January by beating American Tennys Sandgren in the first round.