Andy Murray suffered a loss in Basel, while Cameron Norrie was defeated by Alexander Zverev in Vienna
Tomas Martin Etcheverry of Argentina rallied to win a tough match in Basel, preventing Andy Murray from making it to his first ATP Tour quarterfinal since February.
Murray, 36, overcame a sluggish start to take the opening set in seventy-six minutes.
In the end, though, the world number 32 defeated the British player 6-7 (5-7) 6-3 6-2, winning in more over three hours.
In the meantime, Cameron Norrie's second-round match in Vienna ended in a 6-2, 6-4 loss to Alexander Zverev, the fifth seed.
This season, the former world number one Murray has made it a habit to engage in some lengthy matches; the altercation with Etcheverry was only one such.
After stopping Etcheverry from going up 3-0, the Scot displayed his characteristic endurance and persistence to keep his opponent locked in lengthy rallies during a close opening set that could have gone either way.
Murray was behind in the tie-break but turned it around with an incredible cross-court forehand winner and a smart volley to convert his opportunity.
Murray fell down a break early in the second set, but Etcheverry held strong in a 16-minute seventh game, which was crucial in forcing a deciding. Murray was unable to convert three break points.
After nearly two and a half hours, both players needed a moment to gather themselves before Murray lost another exhausting opening game when he was given a fourth break point.
Murray persisted in applying pressure to the 24-year-old Argentine, but he was unable to generate any more opportunities, which grew increasingly frustrating for him. He frequently threw his racquet onto the ground.
Murray's fourth defeat in five matches and Etcheverry's decisive victory in the last three games completed a miserable evening for the British singles players.
Though he is regarded as the strongest player in the country, Norrie has not been able to consistently challenge Germany's Zverev and has struggled for victories in recent months.
One significant difference was the caliber of serving; Zverev, the runner-up in the 2020 US Open, was consistently accurate and forceful whereas Norrie only landed 54% of his first serves.
Norrie was also concerned about a knee problem. When he trailed 4-3 in the second set, the left-hander requested a medical timeout. Leon Smith, the captain of the British Davis Cup, will also be praying that the issue is not serious.
Smith, who included Norrie in his five-man roster for the November 23 quarterfinal matchup in Malaga versus Serbia, is already waiting anxiously to find out how serious Dan Evans' calf injury from Tuesday is.
After suffering a recent foot injury, Wimbledon winner Carlos Alcaraz thinks he will be ready to compete in the Paris Masters and the season-ending ATP Finals.