British number one Cameron Norrie was knocked out in the first round of the French Open with a five-set defeat by Russian Pavel Kotov.
World number 57 Kotov dominated Norrie in the deciding set to win 4-6 6-3 3-6 7-6 (7-5) 6-2, and record just his second victory in a Grand Slam.
It is the first time Norrie has lost in the opening round of a major since the 2022 Australian Open.
He is one of four Britons to lose in the first round of this year’s tournament. Linda Noskova eliminated Harriet Dart on day two, while Andy Murray and Jack Draper were beaten on day one.
Katie Boulter and Dan Evans, who both play their opener on day three, are the last two Britons in the singles draw.
Norrie has had a difficult build-up to Roland Garros. After reaching the quarter-finals of Indian Wells in March the 28-year-old lost five of his next 10 matches.
The 32nd seed was broken early in the first set and at one stage trailed 4-1 but won five consecutive games to take a 1-0 lead.
In the second set he had two break points saved in the opening game before losing his serve at 5-3 as Kotov rallied.
The pair traded breaks at the start of the third, with 25-year-old Kotov losing his serve late in the set before Norrie held to love to take a 2-1 lead.
Norrie was then broken early in the fourth and at one point trailed 4-1, before recovering to 5-4 down and saving a set point.
In the tie-break he came back from 5-2 down to level but then hit two errors to take the match to a decider.
In the fifth set Norrie was broken in his first two service games as Kotov cruised into the second round for the first time.
Stan Wawrinka, champion in 2015, awaits Kotov next after the Swiss 39-year-old defeated Andy Murray in straight sets on day one.
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