British number one Dan Evans suffered a surprise loss in the Surbiton Trophy second round.
The world number 25 kicked off his preparations for Wimbledon early at the Challenger event in south London, but, after winning his last-32 match on Tuesday, he was beaten in straight sets by Canadian Gabriel Diallo.
The world number 146 won 7-5 6-2 to book a quarter-final place against Jurij Rodionov.
The two-time Wimbledon champion who faces Australian Jason Kubler in Friday’s last-eight tie, is the second seed and will be eyeing his first grass title since winning at SW19 in 2016.
There were mixed results in the women’s ITF tournament, with seven Britons in action.
Isabelle Lacy did not have to go on court to advance as her opponent Sachia Vickery pulled out while Katie Swan was leading 5-3 in the first set when Oceane Dodin retired injured.
Harriet Dart headed out as she lost 6-4 6-7 (5) 6-4 to Tatjana Maria.
