Cameron Norrie suffered a shock second-round loss to French qualifier Corentin Moutet to round out a day of misery for the British men at the Paris Masters.
In a match that did not get underway until after midnight, the 13th-ranked Brit never looked comfortable against his 64th-ranked opponent, falling 6-3 5-7 7-6 (3) in almost three hours on court.
Norrie proved to be his own worst enemy, giving up 27 unforced errors and four double faults while only managing to hit 34 winners, compared to 50 from Moutet.
It came after Norrie’s compatriots Dan Evans and Jack Draper also suffered second-round exits.
Despite some incredibly close games in the second set, Draper was beaten 6-3 7-5 by world number 21 Frances Tiafoe in an hour and 24 minutes.
Tiafoe started well in the opening set, but Draper hit two aces in the fourth game to draw level at 2-2.
Although the American was threatening to pull away, Draper put up a fight in the eighth game, which lasted over 10 minutes, before Tiafoe eventually broke and went on to take the first set.
World number 45 Draper began the second set well, firing down four aces across the first three games, but Tiafoe kept pace with his opponent.
With the scores level at 5-5, the match looked to be heading towards a tie-break, but Tiafoe got the edge on Draper to break in the 11th game before going on to win the second set 7-5.
Tiafoe will face Alex de Minaur in round three after the Australian eclipsed Daniil Medvedev 6-4 2-6 7-5.
Evans was also knocked out of the tournament as he fell 6-3 6-4 to fifth seed Stefanos Tsitsipas.
The world number five displayed his dominance, smashing three aces in the third game to go 3-0 up, before Evans rallied to bring the score to 5-3.
The Greek showed his strength, however, capitalising on a double fault from the the world number 27 in the ninth game to take the first set.
Tsitsipas broke in the first game of the second set, but faced a difficult challenge against Evans, who came back to trail 5-4.
However, Tsitsipas was able to hold on and saw the match out with an ace in the 10th game to progress to round three, where he will face Moutet.
Rafael Nadal also suffered a second-round exit. The second seed was beaten 3-6 7-6 (4) 6-1 by world number 31 Tommy Paul.
Meanwhile, Felix Auger-Aliassime and Andrey Rublev completed the singles field for the 2022 Nitto ATP Finals which is due to be played next week.
The pair will join Nadal, Carlos Alcaraz, Casper Ruud, Tsitsipas, Novak Djokovic and Daniil Medvedev in the season finale.
If the champion at this year’s tournament lifts the trophy without losing a single match, he will earn more than 4.7million US dollars (£4.1m) – which is set to be the largest prize money for an individual player in the history of tennis.
