Katie Boulter crashed out of Wimbledon in the first round to add to the British misery.
The British No2 was second best throughout against Tyra Caterina Grant, who was making her debut in the main draw of a Grand Slam.
The 18-year-old qualifier proved far too good for Boulter in a shock 6-4 6-2 win in a little over an hour.
Boulter hit eight double faults and 21 unforced errors in a ragged display, continuing a dismal showing from the British players at SW19. Grant did not face a single break point in the match.
All ten Brits in action on the opening day were beaten and Boulter was unable to flip the mood early on Tuesday. This was the first time in nine years she has lost in the first round at Wimbledon.
Boulter walked out to a warm reception on Court 3 but the mood started to quickly turn flat as her second serve let her down.
Two double faults in a game gifted Grant, ranked 172nd in the world, a break and a 2-1 lead and that proved to be the decisive moment of the set.
Boulter grew frustrated, both with herself and the technology. When a Grant ace was deemed to be in, Boulter asked for the ball herself to examine for chalk marks, tossing it away and shaking her head.
Grant held to 15 to seal the set and leave Boulter with a mountain to climb.
The comeback never really looked to be on. More double faults from Boulter's racket followed and Grant again broke to move 2-1 in front.
Boulter was error-strewn but Grant more than played her part in piling the pressure on. She looked firmly at home on the grass, producing a sublime drop volley and then a forehand winner to consolidate the break.
One break became two as the match slipped away from Boulter in a hurry. She looped a forehand long to give Grant three break points and the Italian took the second with a powerful pass down the line.
As had been the case throughout the match, Boulter was unable to put any pressure on Grant's serve.
One match point was all Grant needed to secure the biggest win of her career, leaving the court in tears as the magnitude of the occasion dawned on her.
