Andy Murray was knocked out of the US Open in the third round by Italian Matteo Berrettini.
The Scot was trying to reach the last 16 of a Grand Slam for the first time since his hip problems began in 2017.
But he failed in the fourth set, despite the threat of a classic comeback.
Murray, 35, lost the first two sets but fought back in the third, winning it in a tie-break.
Berrettini, however, avoided a decisive fifth set, taking the fourth set.
The Italian won the game 6-4, 6-4, 6-7, 6-3.
Murray had spoken positively about his fitness and movement after dropping just one set in his opening two matches to advance to the third round in New York for the first time since 2016.
But Berrettini is a proven performer at Grand Slams in particular, having reached at least the quarter-finals in the last four majors.
After a close first set, a double fault by Murray on break point in the seventh game gave Berrettini, who is seeded 13th, the first set.
The British number three then recovered from an early break in the second set and appeared to gain the upper hand from the baseline, only to be broken again on a double fault, this time at 4-4.
Murray threw his racquet towards his chair in disgust as he found himself staring down a two-set deficit.
He hadn’t fought back in two sets to win a match since a clash with Yoshihito Nishioka at Flushing Meadows two years ago, which he admitted this week took him months to recover from.
But he managed to stay in the match and won the third set on Friday in a tie-break.
The comeback really seemed to be happening when Murray broke Berrettini’s powerful serve in the opener of the fourth set, but the Italian fought back straight away and another clear from his opponent at 3-4 was the final nail.
Although he couldn’t discover his pre-2017 form, Murray moved up the rankings after slowly regaining form and fitness.
However, it’s been another season where he hasn’t been able to make his mark on the bigger stage and his attention will now turn to the Davis Cup in Glasgow later this month.
Berrettini, who has struggled with injuries this year, is heading to week two of the US Open for the fourth year in a row.
After Murray’s loss, fellow Briton Jack Draper retired injured, leaving Dan Evans and Cameron Norrie as Britain’s only singles hopes at the final major of the year.
Meanwhile, Berrettini will face young Spaniard Davidovich Fokina, who beat Daniel Galan in four sets.
