Andy Murray and Cameron Norrie both suffered first-round exits at the Monte Carlo Masters on Monday, but fellow Briton Jack Draper progressed to the second round.
Draper overcame Argentina's Sebastian Baez in straight sets to advance to the last 32, but either side of the 21-year-old's triumph, Norrie and Murray lost to Francisco Cerundolo and Alex de Minaur respectively.
A couple of weeks on from a first-round exit at the Miami Open, Murray's Masters disappointment continued with a resounding 1-6 3-6 defeat to De Minaur in one hour and 26 minutes.
A plethora of unforced errors had Murray on the back foot from the off, as De Minaur surged into a 4-0 lead during the first set before breaking for a third time to put one foot firmly in the second round.
Sensational comebacks characterised the start of Murray's 2023 season, but the three-time Grand Slam winner could not pull off the improbable on Court Rainier III, where he also clashed with the umpire after he lost a point when his cap fell off.
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While proving effective at the net as ever, Murray was simply outclassed by De Minaur and apologetically held his hands up to the Monte Carlo crowd after bowing out with a whimper.
A few hours before Murray's exit, current British number one Norrie also suffered back-to-back exits at ATP 1000 events, going down 3-6 4-6 to Argentinian Cerundolo in just 72 minutes.
Winning a mere 53% of points behind his first serve compared to Cerundolo's 90%, the world number 13 won just one point in the opening three games of the match, being broken to love in a disastrous start.
The Briton steadied himself and earned one break back in the seventh game, but Cerundolo responded by triumphing in the next two games to take the opening set.
Barring two missed break points for Cerundolo, Norrie noticeably upped his service game in the second set as the duo traded eight successive holds, but world number 33 Cerundolo earned the pivotal break in the ninth game before holding to 15 to advance to round two.
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However, there was something to cheer for the Brits on the Court des Princes, as exciting prospect Draper defeated Baez 6-3 7-5 in one hour and 51 minutes.
The 21-year-old retired from his Indian Wells last-16 clash with Carlos Alcaraz due to an abdominal injury, but he showed few ill effects early doors, winning four of the first five games.
Baez had squandered a 40-0 lead on Draper's serve in the fifth game, and the Brit saved a further two break points while serving out the set before breaking for a 3-2 lead in the second set.
Baez finally converted a break point at the 10th attempt to get the contest back on serve straight away, but he was left to rue untimely mistakes late on, as Draper broke again in the 11th game and saved yet another break point to progress.
Draper will now face Polish 10th seed Hubert Hurkacz in the second round, while Dan Evans takes on Belarus' Ilya Ivashka in his first-round singles match on Tuesday.
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