Andy Murray's run in the US Open came to an end in a four-set defeat to Matteo Berrettini in Friday's third-round battle, while Jack Draper was forced to retire from his battle with Karen Khachanov with a leg injury.
Great Britain began the day with four men in the third round of the Grand Slam tournament for the very first time in the Open Era, but Berrettini quickly ensured that there would not be a quartet of players from the nation in round four.
The first break of the match went the way of Berrettini following a Murray double fault, and the 2012 champion could not hit back before a similar story befell him in the second set.
Berrettini connected with a powerful smash from Murray's defensive lob to immediately go a break up in the second set, but Murray quickly brought the encounter back on serve before another double fault allowed his Italian counterpart to serve out the second set.
Desperately needing to find a second gear to keep his hopes of glory alive, Murray saved numerous break points in the third set and edged the tie-break before a particularly disastrous game handed the initiative to Berrettini.
Murray has become renowned for his comebacks from two sets down during his career, but a couple of failed drop shot attempts and another unforced error handed Berrettini the only break that he needed in set four to eventually get the job done 6-4 6-4 6-7 [1-7] 6-3 with an ace.
© Reuters
There was further heartache for the Brits during Draper's battle with the Russian Khachanov, as the world number 53 - who beat Felix Auger-Aliassime in round two - could not battle through the pain of a leg injury.
World number 31 Khachanov would come out all guns blazing to take the first set with aplomb before Draper levelled the match, and the starlet would further derail the Russian's momentum before being dealt a cruel blow.
Draper would brilliantly go 3-0 up in the third set, but the 20-year-old was then forced to take a medical timeout with an apparent leg issue, which did not stop him from moving one game away from taking the third.
However, Khachanov was not in a sympathetic mood by any stretch and took advantage of Draper's injury to go from 2-5 down to 6-5 up, with the British youngster double faulting three times in one game.
Before Khachanov had the chance to serve for the set, a dejected Draper took the decision to retire from the match and end his promising run at Flushing Meadows, and his third-round exit represents his best-ever run at a Grand Slam.
Khachanov advanced 6-3 4-6 6-5 and will take on either Pablo Carreno Busta or Alex de Minaur in the fourth round, and GB still have Cameron Norrie and Dan Evans hoping to make it into round four as the duo meet Holger Rune and Marin Cilic respectively on Saturday.
Ben Knapton
