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British No 1 Dan Evans suffered a surprise loss in the Surbiton Trophy second round.
The world No 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 No 146 won 7-5 6-2 to book a quarter-final place against Jurij Rodionov.
Evans, who was the first seed at Surbiton, is due to head to the Challenger event in Nottingham next week and his exit opens the draw up for Andy Murray.
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 the All England Club in 2016.
There were mixed results in the women's ITF tournament, with seven Britons in action.
Katie Boulter came from a set down to beat compatriot Sonny Kartal 3-6 6-3 6-4 while Lily Miyazaki won another all-British affair, winning 6-4 7-5 against Eden Silva.
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 (5-7) 6-4 to Tatjana Maria.