Andy Murray was knocked out in the third round of the US Open by Matteo Berrettini, from Italy.
The Scot tried to reach the 16th position in a grand slam for his first grand slam since his hip problems began in 2017.
He fell short of his fourth set goal despite promising a classic comeback.
Murray, 35, lost both sets, but battled back in the third and won it in a tiebreak.
Berrettini won the fourth set, but was unable to decide the fifth set.
The match was won by the Italian 6-4,6-4, 6-7 and 6-3.
Murray spoke positively about his movement and fitness after dropping only one set in the first two matches. He made it to the third round in New York, his first since 2016.
Berrettini, however, is a strong performer at grand Slams. He reached at least the quarter-finals of the four previous major tournaments.
After a close opening set, Murray’s double fault on break point in the seventh set gave Berrettini (ranked 13th) the first set.
After recovering from an early break in set 2, the British number three appeared to be ascendant from the baseline. However, he was again broken by a double fault at 4-4.
Murray was disgusted when he saw a two-set deficit and threw his racket at his chair.
Since a two-set loss to Yoshihito Nishioka two years ago at Flushing Meadows, he had not won a match. He also admitted that this week was difficult for him to recover from.
He managed to keep the game alive and won the third set in a tie-break on Friday.
Murray broke Berrettini’s powerful serve in the first game of the fourth set. However, the Italian player immediately responded and he hit back at Murray. The final nail was a lapse by his opponent at 3-4.
Murray is slowly returning to his pre-2017 form but he has not been able find it.
It is yet another season in which he has not been able to make an impact on the biggest stage. His attention now turns to the Davis Cup in Glasgow later in the month.
Berrettini has been having problems with injuries this year and makes it to week 2 of the US Open for the 4th year running.
Murray’s loss left Jack Draper, a fellow Brit, to retire from injury. Dan Evans and Cameron Norrie were the only British singles hopefuls at the final major.
Berrettini will now play Davidovich Fokina from Spain, who defeated Daniel Galan in just four sets.