British number one Cameron Norrie crashed out of the Paris Masters in the second round after losing in three sets to French qualifier Corentin Moutet.
Following Dan Evans and Jack Draper's eliminations earlier in the day, Norrie was the last British man left standing in the singles tournament when he faced off against Moutet deep into the night.
Despite a brief second-set fightback and a tense final-set tie-break, Norrie went down 3-6 7-5 6-7[3] to Moutet in two hours and 52 minutes as GB's run in the men's singles came to an end.
Norrie was broken in the fifth game of the first set after a spate of unforced errors, and while serving to stay in the set, he missed a game point at 40-30 up as Moutet broke for a second time.
The second set would be a much tighter battle, and Norrie stormed to a 40-0 lead in the 11th game to bring up three break points, and he took the first of them before holding to love and forcing a third-set decider.
© Reuters
However, it was now the Frenchman's turn to break to love as Norrie went 3-1 down, but the 27-year-old immediately earned the break back to get the contest back on serve.
Moutet squandered one more break point before the match went all the way to a winner-takes-all tie-break, and a couple more unforced errors bedevilled Norrie as the 12th seed crashed out.
The British number one produced four double faults and only won 31% of points on his second serve, while Moutet hit 50 winners on the day and advances to face Stefanos Tsitsipas in round three.
Tsitsipas also came up against British opposition in the form of Evans, and the Greek fifth seed took just one hour and 20 minutes to wrap up a comprehensive 6-3 6-4 victory.
Evans was broken in his first service game in the opening set - despite Tsitsipas missing two of the three break points he had brought up - and the Greek also broke straight away in set two.
© Reuters
Evans had to beat away a couple more break points before the duo remarkably played out four successive love holds, which worked in Tsitsipas's favour as he knocked the 32-year-old out, but there were only 15 unforced errors between the pair.
Finally, 20-year-old sensation Draper pitted his wits against US Open semi-finalist Frances Tiafoe in the second round, and the youngster was also eliminated in straight sets 3-6 5-7 in one hour and 24 minutes.
In a match where the aces were flying in for both players, Tiafoe missed two chances to break in the eighth game before eventually managing to do so, but Draper then squandered two of his own in the next game to cede the first set.
Failure to convert break points would prove to be Draper's downfall, as he wasted five in the second set before Tiafoe broke on an unforced error from the Brit in the 11th game.
Having moved a set and a break up, Tiafoe - who saved all seven break points he faced on the day - produced his seventh ace before holding to love and setting up a clash with Alex de Minaur.
Ben Knapton
