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Jack Draper was beaten by Dutch qualifier Jesper de Jong as the British campaign at the French Open got off to an inauspicious start.
Draper, 22, is 35th in the world but lost 7-5 6-4 6-7 (3-7) 3-6 6-3 to 176th-ranked De Jong on day one at Roland Garros.
The British number two struggled on serve and was broken nine times as De Jong punished him.
He made too many unforced errors and showed his frustrations after a double fault handed over a 5-3 fifth-set lead to De Jong, who served out after four hours six minutes for the biggest win of his career.
Draper was the first of six British players to step out on to the Roland Garros dirt, with Andy Murray being the second later on Sunday.
Murray makes his return to the tournament - having not played there since 2020 - against fellow three-time major champion Stan Wawrinka in the night session on Court Philippe-Chatrier.
Murray, 37, could be playing at Roland Garros for the final time, having indicated he is likely to retire later this year.
Four other Britons - Katie Boulter, Cameron Norrie, Dan Evans and Harriet Dart - play their opening matches on Monday and Tuesday.
Draper is a fine talent with ambitions of reaching the world's top 10, but this defeat was another example of the work he still has to do.
The left-hander recently brought South African former world number nine Wayne Ferreira into his coaching team to help achieve his goal, saying before he faced De Jong that his game - particularly his serve - is “in transition”.
Only landing 50% of his first serves, and winning just 51% of second-serve points, were indicative of that.
Double faults also came at costly moments, none more than the one at 30-40 in the seventh game of the decider which helped De Jong secure victory.
De Jong, 23, oozed confidence on the clay following his three qualifying victories to reach the main draw, while Draper lacked certainty.
After losing a tight first set by being broken in the 12th game, Draper improved to lead 4-2 in the second but lost his way again as De Jong won the final four games of the set.
None of Draper's seven previous defeats in a Grand Slam main draw had come in straight sets.
While Draper showed plenty of fight to avoid that, his level was still not there and allowed De Jong off the hook with some passive returning in the rallies.
A fine forehand winner down the line arrived at a timely juncture in the tie-break, putting him 5-3 ahead before a double fault and backhand into the net from De Jong continued the match.
Draper found his groove to move a break up in the fourth and, after a hour-long rain delay, took the match into a decider.
Only once had the Briton played a five-set match - when he came through to beat Marcos Giron in brutal conditions at this year's Australian Open.
That felt like a landmark moment in Draper's career, showing he had built up the physical and mental resilience to overcome adversity.
However, Draper was unable to win another Grand Slam decider as De Jong set up a second-round meeting with Spanish third seed Carlos Alcaraz.