Andy Murray fell to an early exit at the Monte Carlo Masters as he lost to Alex de Minaur in the first round.
British number three Murray, currently ranked 57th in the world, was beaten 6-1 6-3 by the Australian 14th seed.
Murray, a three-time Grand Slam champion, was playing on the Monaco clay for the first time since 2017.
Earlier, British number one Cameron Norrie was also knocked out in the first round but Jack Draper returned from injury with a win.
In total, Murray committed 26 unforced errors compared to the eight of De Minaur, who will face Germany’s Jan-Lennard Struff in the second round.
De Minaur was yet to win a Masters 1,000 match this year after opening defeats at both Indian Wells and Miami, but rectified that with his third victory over Murray on the ATP Tour.
While both players were making their first appearance on clay in 2023, Murray – on his least favourite surface – was far from his best, losing the opening four games as De Minaur romped to the first set in 35 minutes.
After arguing with chair umpire Carlos Bernardes early in the second set because he did not stop play after Murray’s cap fell off mid-point, the Scot further lost his way, broken in the next game amid numerous unforced errors before De Minaur saw out a comfortable win.
Earlier on Monday, Norrie, ranked 13th in the world, was beaten 6-3 6-4 by Argentina’s Francisco Cerundolo.
In his match, Norrie looked unsettled throughout and had 18 unforced errors compared with only eight winners.
World number 33 Cerundolo, 24, gained the decisive break in the ninth game of the second set when 27-year-old Norrie netted a forehand.
Norrie started the season with a run of 21 wins from 25 matches but also lost his opening match at the Miami Open last month when he was defeated by France’s Gregoire Barrere.
Fellow Briton Draper beat another Argentine, Sebastian Baez, 6-3 7-5 to set up a second-round meeting with 10th seed Hubert Hurkacz of Poland.
Draper, 21, was forced to retire during a fourth-round match with world number two Carlos Alcaraz in Indian Wells last month because of an abdominal problem. He then pulled out of the Miami Open as he did not want to make the problem worse.
He was given a strong test against Baez in Monte Carlo but saved 11 of the 12 break points he faced while taking three of his own four chances.
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