British participation in the men’s singles came to an end on day five at Wimbledon with painful defeats for Andy Murray, Cameron Norrie and Liam Broady.
The trio exited the tournament within a 90-minute window on a Friday evening that also saw victories for French Open champions Novak Djokovic and Iga Swiatek on Centre Court.
Carlos Alcaraz and Aryna Sabalenka, two of the favourites for the respective singles titles at the All England Club, were the other notable winners on a bumper day of the Championships where temperatures hit 29C.
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British hopes were high heading into day five, with Murray two sets to one up against Tsitsipas, Cameron Norrie set to face the unseeded Chris Eubanks and Liam Broady on a high ahead of facing 26th Denis Shapovalov.
Amid plenty of twists and turns, that hope turned to despair when each home favourite exited Wimbledon between 5.59pm and 7.29pm.
Norrie suffered the first knockout blow, going down to the canvas and never getting back up in four sets to Eubanks before Murray endured five-set heartbreak 18 minutes later.
Broady wrapped up the hour-and-a-half of pain as he missed the chance to serve for a two set to one lead before eventually losing in four.
It means Katie Boulter, who teamed up with boyfriend Alex De Minaur to good success in the mixed doubles on day five, remains the latest British singles’ player in the tournament.
And she faces the small task of trying to take out the defending champion Elena Rybakina on Centre Court on Saturday.
Alcaraz matches Nadal record as reigning champion scrapes into Madrid Open quarters
Jan-Lennard Struff made life difficult for Carlos Alcaraz, but the reigning Madrid Champion eventually made it through.
Alcaraz had won both of his opening games with the minimum of fuss, but he needed three sets to get beyond Struff, who won a second-set tie-break.
However, Alcaraz eventually prevailed in the decider, clinching a 6-3 6-7 (5-7) 7-6 (7-4) victory.
Alcaraz, who is in the hunt for a third straight title in Madrid, will now face seventh-seed Andrey Rublev for a place in the last four.
Data Debrief: Prodigal son matches the master
There have been plenty of comparisons between Alcaraz and his fellow Spaniard Rafael Nadal.
And with his win on Tuesday, Alcaraz matched Nadal's record for the longest winning run at the Madrid Open, at 14 matches, since the tournament began in 2002.
Sinner fights back to reach first Madrid Open quarter-final
Jannik Sinner has booked his place in the Madrid Open quarter-final, going the distance to beat Karen Khachanov 5-7 6-3 6-3 on Tuesday.
The top seed dropped a set for the first time at the tournament as an in-form Khachanov, but he shook off the concerns of a lingering hip injury to make a comeback.
After winning the second set, he then saved both break points he faced in the decider, finishing off a contest that lasted over two hours.
Sinner has reached the quarter-final of the Madrid Open for the first time and will face either Casper Ruud or Felix Auger-Aliassime next.
Data debrief: Sinner overcomes first big test
Not only has the 22-year-old become the only player to reach the quarter-final at all four Master 1000 events in 2024, but he is the first to achieve that feat since Milos Raonic in 2016.
Sinner has also become the first Italian player to make the quarter-finals of all three existing ATP Masters 1000 events on clay, since 2009 when the Madrid Open took the place of the Hamburg Masters.
Swiatek battles back to reach Madrid Open semi-finals
Iga Swiatek has booked her place in the Madrid Open semi-finals after battling back from a set down to defeat Beatriz Haddad Maia.
The top seed, who made it to the final last year, dropped a set for the first time in this tournament before recovering to win 4-6 6-0 6-2 in a match that lasted just short of two-and-a-half hours.
These two players met in the French Open semi-finals last year and 11th seed Haddad Maia was eyeing an upset when she fought back from 4-1 down to claim the opener.
But Swiatek dropped serve just once in the next two sets as she assumed full control and swept to victory, powered by winning eight straight games from the start of the second set.
Data Debrief: Swiatek statistics up there with the best
Up next for Swiatek will be a last-four clash against either Ons Jabeur or Madison Keys, who play later on Tuesday. That will be her 15th WTA 1000 semi-final appearance since 2020, with no other player having made it to double figures (Aryna Sabalenka and Maria Sakkari are the next best on eight each).
Beating Haddad Maia also means Swiatek has equalled Serena Williams and Maria Sharapova as the fastest player to reach 25 WTA 1000 wins on clay, doing so in just 29 matches.
And Swiatek's emphatic second set saw her tie Coco Gauff for the most number of 6-0 sets won so far this year. They both have seven, just ahead of Sabalenka (five).
Defending champion Sabalenka plays Mirra Andreeva in the last eight on Wednesday after battling past Danielle Collins in three sets. All three of her wins so far have been in deciding sets.
The other last-eight clash is between Elena Rybakina and Yulia Putintseva.
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