Andy Murray was knocked out of the US Open in the third round by Matteo Berrettini of Italy.
The Scot has attempted a Grand Slam round of 16 for the first time since his hip problems began in 2017.
But he failed in the fourth set, despite threatening a classic comeback.
Murray, 35, lost the first two sets but fought back in the third, winning the first half.
However, Berrettini avoided the fifth deciding game, after the fourth.
The Italians won with a score of 6-4, 6-4, 6-7, 6-3.
Murray spoke positively about his fitness and movement after dropping just one set in his first two games to make it through to the third round in New York for the first time since 2016.
But Berrettini is a proven artist at Grand Slams in particular, having reached at least the quarterfinals in the last four major tournaments.
After a tight opening set, a double error from Murray on the break point in the seventh game went to Berrettini, who is ranked 13th, in the first set.
The British number three then recovered from an early break in the second set and appeared to have bounced off the bottom line, only to be broken again by a double error, this time 4-4.
Murray threw his racquet toward his chair in disgust as he found himself staring into the distance two sets.
He hasn’t hit back from two sets to win a single match since his clash with Yoshihito Nishioka at Flushing Meadows two years ago, something he admitted this week took him months to recover from.
But he managed to stay in the game and won the third set on Friday in a draw.
The real comeback came when Murray broke Berrettini’s powerful serve in the opening match of the fourth set but the Italian hit back immediately and another long shot by his opponent with a score of 3. -4 is the final nail.
While he may not have discovered his form before 2017, Murray has returned to the rankings after slowly regaining form and fitness.
It’s been another season, though, where he hasn’t been able to make his mark on the biggest stage and his attention will now turn to the Davis Cup in Glasgow later this month.
Berrettini, who has been troubled with injury this year, reached the second week of the US Open for the fourth year in a row.
Following Murray’s loss, fellow Brit Jack Draper retired from injury, leaving Dan Evans and Cameron Norrie the only hope of British singles at the year’s final major.
Meanwhile, Berrettini will face young Spaniard Davidovich Fokina, who beat Daniel Galan in four sets.
