Dan Evans' grass-court campaign took an early blow as he suffered a surprise defeat in the second round of the Surbiton Trophy.
The British number one was beaten 7-5 6-2 by Canada's world number 146 Gabriel Diallo.
Top seed Evans had started his Wimbledon preparations early at the south London Challenger event after his first-round exit at the French Open.
Andy Murray, seeded second, plays in the quarter-finals on Saturday.
Elsewhere in Thursday's action, there were mixed results for Britain's women with Katie Boulter and Lily Miyazaki among those advancing to the quarter-finals.
Boulter, who could replace the injured Emma Raducanu as British number one next week, defeated compatriot Sonay Kartal 3-6 6-3 6-4, while Miyazaki beat Eden Silva 6-4 7-5 in another all-British affair.
Isabelle Lacy also progressed to the last eight without hitting a ball after her opponent Sachia Vickery withdrew, while Katie Swan advanced after Oceane Dodin retired injured with the Briton 5-3 up in the first set.
But there was defeat for British number four Harriet Dart, who lost 6-4 6-7 (5-7) 6-4 to Germany's Tatjana Maria.
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