Cameron Norrie lost as Britain’s interest in the Wimbledon men’s singles ended, while Harriet Dart was unable to make the women’s fourth round for the first time.
Norrie, 28, was beaten 6-4 6-4 7-6 (17-15) by German fourth seed Alexander Zverev.
Zverev, who has never gone past the last 16 at the All England Club, battled through after sustaining a knee injury early in the second set.
The 27-year-old could not take his first five match points in a monumental tie-break, where Norrie also had five set points, before clinching victory at the sixth attempt.
Shortly afterwards on Saturday, 27-year-old Dart lost 2-6 7-5 6-3 to China’s Wang Xinyu.
Dart looked close to tears after letting a 3-0 lead slip in the deciding set.
The British women’s number two was attempting to reach the last 16 of a Grand Slam for the first time.
While Dart became emotional, China’s Wang remained composed to wrap up victory in a rain-disrupted encounter.
Norrie and Dart’s defeats mean Emma Raducanu, who beat Greek ninth seed Maria Sakkari on Friday, is the only Briton remaining in the singles.
Recently being deposed as the British men’s number one was the result of a chastening few months for 42nd-ranked Norrie.
A promising start to the season, including reaching the Australian Open fourth round where he lost a bruising battle with Zverev, was derailed by illness in Rio de Janeiro and he has struggled for form since.
Coming into Wimbledon, Norrie had suffered first-round exits at Roland Garros, Queen’s and Eastbourne.
A surprise defeat by British world number 773 Jack Pinnington Jones at an ATP Challenger event in Nottingham was sandwiched between the home events.
But Norrie has found his game again at Wimbledon, where he reached the semi-finals in 2022.
“I’ll take it, the grass season ending like this. I felt like I played my best tennis at the end,” Norrie said.
“Obviously it’s not the result I wanted today, but the level I played, the level of concentration, the way I was hitting the ball and moving. My body feels in really good shape and it was a really positive Wimbledon for me.”
A pumped-up Norrie gave a reminder of his quality by beating Jack Draper, who has unseated him as the leading British man, in the second round.
Zverev is arguably the finest current men’s player not to have won a Grand Slam title – an unwanted moniker retained following his loss to Spain’s Carlos Alcaraz in last month’s French Open final – and was a different proposition.
Zverev used his huge serve and classy backhand to great effect, pinning Norrie behind the baseline and not allowing the Briton to turn defence into attack.
A single break for a 3-2 lead proved enough for the German to take the opening set.
But there was a concerning moment early in the second set when Zverev jarred his left leg chasing a drop shot and clattered into the net in front of the umpire.
The incident left the majority of the Centre Court crowd – including Olympic champions Sir Chris Hoy and Dame Jessica Ennis-Hill, plus Manchester City manager Pep Guardiola, as part of Sporting Saturday – gasping in concern.
Zverev looked in agony as he stayed down on the grass.
After eventually getting up and receiving treatment, he was able to continue but did not look comfortable as he moved around gingerly.
His movement improved as the set wore on, breaking again in the ninth game before coming through a 26-minute tie-break.
In her second-round win over British number one Katie Boulter, Dart became tearful in the final-set tie-break before fighting her way back from 6-2 down.
Emotions came to the forefront for Dart once more against Wang, but she was unable to compose herself this time and she shook hands with the world number 42 with her hands covering her eyes.
“To be up in two sets and come away with a loss is pretty heartbreaking to be honest,” said Dart.
“I had a 3-0 lead in the third and I lost six games in a row so I only have myself to blame.
“This one will definitely sting for a long time.”
Taking to the court two hours later than scheduled because of the weather, Dart and Wang were only playing for 25 minutes before the rain returned.
When play resumed after more than an hour’s break, Dart held a 3-1 lead and needed just 13 minutes to cruise through the rest of the set and take control.
Contending with blustery conditions on court two, the pair traded breaks in the second set and Dart saved two set points before Wang forced a decider.
The Briton raced to a 3-0 lead, but frustration crept in and Dart angrily whacked a ball into the court as Wang clawed her way back and momentum shifted.
Wang will play in the last 16 of Wimbledon for the first time when she will face two-time finalist Ons Jabeur or Ukraine’s Elina Svitolina in the last 16.