Katie Boulter produced a gutsy display against Ashlyn Krueger but failed to serve out for the match as she was beaten in the second qualifying round for the French Open.

On a difficult day for Britons attempting to progress into the Roland Garros main draw, Boulter joined Harriet Dart, Fran Jones, Liam Broady, Ryan Peniston and Jan Choinski in losing in Paris on Wednesday.

It means only Cameron Norrie, Dan Evans, Kyle Edmund and Jack Draper will fly the flag for Britain in the second major of 2023, following Andy Murray’s withdrawal and Emma Raducanu’s recent fitness woes.

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Boutler had been seeded 24th for qualifying but lost out 2-6 6-2 6-7 (6) to Krueger after a lengthy battle.

American Krueger claimed the opener before Boulter hit back to level, but then quickly found herself 5-2 down in the third set.

The British number three fought back to reel off four consecutive games to give herself the chance to serve out and progress into the final qualifying round but Krueger forced the tie-breaker.

It was then the teenager from Missouri, who had beaten Lily Miyazaki on Tuesday, who held her nerve to set up a third qualifying round meeting with Storm Sanders.

Boulter’s fellow British hopeful Jones saw her aspirations of making a first French Open appearance end after she had to retire during her match with Ylena In-Albon.

Jones, who suffers from a congenital condition which means she has three fingers and a thumb on each hand, three toes on one foot and four toes on the other, was left in tears as she had to retire due to an apparent shoulder injury when 4-1 down during the first set.

Dart also exited in the second qualifying stage after she was beaten by France’s Elsa Jacquemot 1-6 6-1 6-2.

It meant the trio joined Heather Watson, Katie Swan, Sonay Kartal and Miyazaki in failing to qualify for the French Open meaning there will be no British female involved in the singles’ event at Roland Garros.

Broady, the British male number five, also suffered defeat on the clay on Wednesday but only following a back and forth clash with Emilio Nava.

Broady lost an even opener before he hit back in style to inflict a bagel on Nava in the second. American Nava regrouped though and clinched the third to progress 6-4 0-6 6-3.

World number 191 Peniston was another to be edged out in third following a 2-6 6-2 6-4 loss to Romanian eighth seed Radu Albot.

Meanwhile, Choinski was beaten 3-6 6-4 6-0 by Sebastian Ofner.