Great Britain's campaign at the French Open got off to an inauspicious start as Jack Draper lost to Dutch qualifier Jesper de Jong.
The 22-year-old Draper, ranked 35th in the world, lost 7-5, 6-4, 6-7 (3-7), 3-6, 6-3 to de Jong, ranked 176th in the world, on the opening day of Roland Garros.
The British number two struggled on his serve and was broken nine times by de Jong.
He made too many unforced errors and showed his frustration after a double fault to hand a 5-3 fifth set lead to de Jong, who served out the match in four hours and six minutes for the biggest win of his career.
Draper was the first of six British players to step onto the dirt at Roland Garros, with Andy Murray becoming the second after Sunday.
Murray has not played in the tournament since 2020 but will return to the tournament when he takes on fellow three-time Grand Slam champion Stan Wawrinka in the night session on Court Philippe Chatrier.
The 37-year-old Murray has signalled he is likely to retire later this year, potentially making this his final time playing at Roland Garros.
Four other British players – Katie Boulter, Cameron Norrie, Dan Evans and Harriet Dart – will play their opening matches on Monday and Tuesday.
Frustrated, Draper still has work to do.
Draper is an incredible talent with aspirations of breaking into the world's top 10, but this loss was another example of the work he still has to do.
The left-hander recently brought in South African former world number 9 Wayne Ferreira to join his coaching staff to help him achieve his goals and said before the match against de Jong that his game, particularly his serve, was “in transition”.
That's evident in the fact that he was successful on just 50 percent of his first serves and won just 51 percent of his second serve points.
The double faults came at crucial moments, particularly at 30-40 in the seventh game of the deciding match, which helped De Jong win the match.
“My serve has been an issue this year and I'm trying to change it to get better,” Draper said.
“Right now I'm not confident with my serve. It's something I need to improve on. I'm really disappointed.”
While Draper struggled, the 23-year-old de Jong showed confidence after winning three consecutive qualifying matches to advance to the main draw.
De Jong kept the first set close by breaking Draper's play in the 12th game, then won the final four games of the set.
Draper has lost seven times in the main draw of a Grand Slam, but none of them were in straight sets.
A down-the-line forehand winner just in time in the tiebreaker gave Draper further progress, earning a break in the fourth set and sending the match to a decider after an 80-minute rain delay.
The only other time the Briton played a five-set match was when he beat Marcos Giron in tough conditions at the Australian Open this year.
It felt like a landmark moment in Draper's career, demonstrating the physical and mental resilience he has developed to overcome adversity.
However, Draper was again unable to win a Grand Slam final, and de Jong will face third seed Carlos Alcaraz of Spain in the second round.
“[Last year] “I couldn't last nearly three sets and that's probably the longest match I've ever played,” Draper said.
“I didn't have any cramps. I didn't collapse. It wasn't a fitness issue today, it was a tennis issue. So I think that's a real positive.”
