Stefanos Tsitsipas crashed out of the Vienna Open after losing in a dramatic third-set tie-break against Borna Coric, who claimed his third successive win over the Greek ace.
The second seed was the highest-profile casualty in the Austrian capital on Thursday, as he succumbed to the Croatian once more 4-6 6-4 7-6 (7-4).
Coric rescued six match points before stunning Tsitsipas at the 2020 US Open, while he also triumphed when they collided in the Cincinnati showpiece in August.
The world number 27's chances of completing a hat-trick of victories appeared bleak at a set and break down, but he rallied to force a decider that went the distance, before holding his nerve for another notable win.
Coric's reward is a quarter-final clash with Hubert Hurkacz, who boosted his chances of qualifying for next month's ATP Finals with a 7-5 4-6 6-3 win over Emil Ruusuvuori.
Daniil Medvedev advanced to the last eight after a 6-3 6-3 victory over home favourite Dominic Thiem. Next up for the top seed is Jannik Sinner after the Italian saw off Francisco Cerundolo 7-5 6-3.
Third seed Andrey Rublev's ATP Finals hopes were dented after a 6-3 6-4 defeat by Grigor Dimitrov, who will play Marcos Giron after the American overcame seventh seed Cameron Norrie in straight sets.
Over in Basel, third seed Felix Auger-Aliassime required just 49 minutes to complete a commanding 6-1 6-0 rout of Miomir Kecmanovic for his 10th straight ATP win.
Meanwhile, Stockholm champion Holger Rune continued his momentum by recording a seventh straight victory after seeing off Ugo Humbert 6-4 6-2.
Sixth seed Roberto Bautista Agut enjoyed a straight-sets win over three-time grand slam champion Andy Murray to set up a clash with home favourite Stan Wawrinka, who outlasted Brandon Nakashima in a deciding set.
French Open day 12: Karolina Muchova reaches first grand slam final after upset
Karolina Muchova produced one of the shocks of the French Open by upsetting Aryna Sabalenka to reach her first grand slam final.
Muchova came from 5-2 down in the final set, saving a match point, to win 7-6 (5) 6-7 (5) 7-5 and will take on defending champion Iga Swiatek, who survived her first test, beating Beatriz Haddad Maia 6-2 7-6 (7).
Miyu Kato found Paris redemption in the mixed doubles, winning the title with German Tim Puetz after her disqualification from the women’s doubles.
Picture of the dayStat of the dayTweet of the dayQuote of the dayWho’s up next?The men’s finalists will be decided at Roland Garros on Friday.
The blockbuster match comes first up when world number one Carlos Alcaraz meets Novak Djokovic for only the second time in a generational clash for supremacy in the men’s game.
The second encounter, meanwhile, sees Casper Ruud trying to make a second final in two years against Alexander Zverev, whose semi-final here last year against Rafael Nadal ended with him leaving the court in a wheelchair.
Top seed Dan Evans suffers shock second-round exit at Surbiton
Andy Murray is the only British man left in singles at the Lexus Surbiton Trophy after Dan Evans suffered a shock second-round loss.
Evans was the top seed after taking a late wild card following his early French Open defeat but was toppled 7-5 6-2 by 21-year-old Canadian Gabriel Diallo, ranked more than 100 places below him.
It has been a difficult season so far for 33-year-old Evans, who will hope to fare better in Nottingham next week, where he is the defending champion.
There is a lot more home representation in the women’s draw, where Katie Boulter needs one more victory to overtake Emma Raducanu as British number one.
The eighth seed battled to a 3-6 6-3 6-4 victory over countrywoman Sonay Kartal to reach the quarter-finals, where she will face Swiss Viktorija Golubic.
Boulter was joined in the last eight by Isabelle Lacy, Katie Swan and Yuriko Miyazaki.
Sixteen-year-old Lacy was given a walkover by American Sachia Vickery and will play Miyazaki, who defeated compatriot Eden Silva, while Swan was 5-3 up on Oceane Dodin when the Frenchwoman retired.
Harriet Dart was close to joining them but lost a tight tussle 6-4 6-7 (5) 6-4 to top seed and last year’s Wimbledon semi-finalist Tatjana Maria, who next plays Swan.
Shoulder injury rules Jack Draper out of Wimbledon
Jack Draper will miss Wimbledon with the shoulder injury he suffered at the French Open last week.
It is a huge blow to the 21-year-old, whose progress has been disrupted by a series of injuries.
The latest came in practice ahead of his first-round clash at Roland Garros last Monday against Tomas Etcheverry, with Draper forced to serve underarm before calling it a day after only one game of the second set.
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While hugely disappointed that his body had again let him down, Draper was optimistic the problem with his left shoulder would not disrupt his grass-court campaign too much.
However, having had a scan and seen a specialist, Draper has decided to miss the whole of the British summer season.
Draper wrote on Instagram: “It’s clear my shoulder is going to need time and rehab to get back to where it needs to be. My team and I have made the difficult decision to miss the grass court season this year.
“I guess in this sport there are so many ups and downs but this one is tough to take. The only thing for sure is that I will keep persevering.”
He is optimistic he will not need surgery and is hoping to return to the match court in mid to late July.
When he has been fit, Draper has shown he has the potential to be among the best in the world but that has not been nearly as often as he would have liked.
Last season a promising run to the third round of the US Open was ended by a leg injury and, after illness disrupted his pre-season, Draper has already missed large chunks of this year with hip and abdominal problems.
In Paris last week the Londoner said he felt “mentally destroyed”, adding: “I hate being the guy who is injured a lot.”
Draper made his Wimbledon debut in 2021, losing to Novak Djokovic, while last year he pushed Alex De Minaur to four sets in the second round.
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