British number one Cameron Norrie said he is “devastated” after he was knocked out in the first round of the French Open by Russian Pavel Kotov.
World number 57 Kotov beat Norrie in five sets 4-6 6-3 3-6 7-6 (7-5) 6-2 to 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.
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.
“For the first four sets I was in control,” Norrie added. “I had so many chances and he played better than me in the tie-break and deserved to win the fifth.”
Stan Wawrinka, champion in 2015, awaits Kotov next after the Swiss 39-year-old defeated Andy Murray in straight sets on day one.
British number two Dart produced a valiant effort against Czech 27th seed Noskova but ultimately fell to a 7-6 (7-3) 6-4 defeat.
Dart, whose only other French Open appearance was a first round loss in 2022, was broken early by her teenage opponent and defended a set point at 5-4 before breaking back to force a tie-break.
The 27-year-old broke Noskova at the start of the second set, but the Australian Open quarter-finalist won the final three games and will now meet either Argentine Julia Riera or Irina-Camelia Begu of Romania in the next round.
Dart has not won in a Grand Slam since she reached the second round of the 2022 US Open.