Andy Murray is the only British man left in singles at the Lexus Surbiton Trophy after Dan Evans suffered a shock second-round loss.
Evans was the top seed after taking a late wild card following his early French Open defeat but was toppled 7-5 6-2 by 21-year-old Canadian Gabriel Diallo, ranked more than 100 places below him.
It has been a difficult season so far for 33-year-old Evans, who will hope to fare better in Nottingham next week, where he is the defending champion.
There is a lot more home representation in the women’s draw, where Katie Boulter needs one more victory to overtake Emma Raducanu as British number one.
The eighth seed battled to a 3-6 6-3 6-4 victory over countrywoman Sonay Kartal to reach the quarter-finals, where she will face Swiss Viktorija Golubic.
Boulter was joined in the last eight by Isabelle Lacy, Katie Swan and Yuriko Miyazaki.
Sixteen-year-old Lacy was given a walkover by American Sachia Vickery and will play Miyazaki, who defeated compatriot Eden Silva, while Swan was 5-3 up on Oceane Dodin when the Frenchwoman retired.
Harriet Dart was close to joining them but lost a tight tussle 6-4 6-7 (5) 6-4 to top seed and last year’s Wimbledon semi-finalist Tatjana Maria, who next plays Swan.