Emma Raducanu became the third successive major winner to lose to Anhelina Kalinina as the Ukrainian reached her maiden WTA 1000 quarter-final at the Madrid Open.
Ninth-seed Raducanu was the biggest name in action on Tuesday and had been hoping to rack up three successive WTA Tour victories for the first time since her incredible US Open success in September last year.
But Kalinina, who saw off Sloane Stephens and Garbine Muguruza in her two previous matches, got the better of the Brit in an entertaining 6-2 2-6 6-4 win.
Raducanu had not dropped a set in either of her first two outings in Madrid but Kalinina quickly put an end to that.
While the teenager responded well in the second, getting an important break to make it 3-1, Kalinina rallied again in what was a closer deciding set.
The pair traded breaks and then Kalinina got another to set her en route to victory at 5-4 – she had to save one more break point but did ultimately see off Raducanu to book a clash with Jil Teichmann in the last eight.
Teichmann beat Elena Rybakina earlier in the day, dispatching the 16th seed in impressively comfortable fashion as she won 6-3 6-1.
Progression from the last eight for Teichmann will see her reach the semi-final of a WTA 1000 event for the first time.
Sara Sorribes Tormo, the last Spaniard left in the draw, defeated Daria Kasatkina 6-4 1-6 6-3 in something of a rollercoaster ride to line up a quarter-final contest with 12th seed Jessica Pegula.
The American kept her focus despite opponent Bianca Andreescu needing a medical timeout and rain causing a 30-minute halt, eventually winning 7-5 6-1.
Alcaraz lauds 'beast' Sinner after winning China Open classic
Carlos Alcaraz described Jannik Sinner as "a beast" and the world's best player after downing the Italian in Wednesday's remarkable China Open final.
Alcaraz and Sinner battled it out for over three hours in the Beijing showpiece match, with Alcaraz eventually triumphing 6-7 (6-8) 6-4 7-6 (7-3).
The Spaniard took the decisive tie-break with a remarkable run of seven straight points, having lost a tie-break in the opening set to fall behind.
At the age of 21 years and 150 days, Alcaraz is the youngest player to defeat the world number one in an ATP event final after losing the opening set since Juan Martin del Potro (20 years, 356 days), who came back to beat Roger Federer at the US Open in 2009.
Speaking after his sixth career win over the Italian (four defeats), Alcaraz outlined his belief he had overcome the very best in the sport.
"He could have won in two, I could have won in two, he could have won in three. It was a really close match," said Alcaraz.
"Jannik, once again, he showed that he's the best player in the world, at least for me.
"The level that he's playing, it's unbelievable. It's a really high quality of tennis. His shots, physically, mentally... he's a beast."
Sinner breezed into a 3-0 lead in the third-set tie-break, only for Alcaraz to show extraordinary resilience to maintain his 100% record against Sinner this year, having previously beaten him at Indian Wells and Roland Garros.
"I never lost hope. Honestly I knew that every tie-break Jannik plays is almost on his side," Alcaraz said of the decider.
"I thought that in the third set, I'm not going to lie down after two mini-breaks for him. I thought, 'okay, I have to give everything that I have just to try to give myself the opportunity to be close'.
"During the whole week I've been playing great tennis. Probably sometimes the luck went to my side a little bit in the matches."
Alcaraz topples Sinner in China Open epic
Carlos Alcaraz struck seven successive points in a deciding tie-break to seal a remarkable victory over world number one Jannik Sinner in the China Open final.
The leading lights of tennis' next generation of stars battled it out for well over three hours in Beijing on Wednesday before Alcaraz finally prevailed 6-7 (6-8) 6-4 7-6 (7-3).
Having cruised into a 5-2 lead in the opening set, Alcaraz wobbled to allow defending champion Sinner to reel off four of the next five games to force a tie-break that the Italian won with three breaks of serve.
An hour-long second set was settled in Alcaraz's favour, but a topsy-turvy decider went the distance.
Having given up the first break, Sinner responded by hitting back in game eight to restore parity, with another tie-break required.
Sinner breezed into a 3-0 lead, only for Alcaraz to string together an extraordinary run of seven straight points to claim the crown.
Data Debrief: King Carlos
It is now 6-4 to Alcaraz in the head-to-head between the Spaniard and Sinner.
Alcaraz has now won all three of their matches this season, triumphing previously at both Indian Wells and Roland-Garros. It is the first time either of the duo has won three straight matches against the other.
At the age of 21 years and 150 days, Alcaraz is the youngest player to defeat the world number one in an ATP event final after losing the opening set since Juan Martin del Potro (20y 356d), who came back to beat Roger Federer at the US Open in 2009.
Injury forces Osaka out as Gauff progresses at China Open
Naomi Osaka was forced to retire from her China Open meeting with Coco Gauff due to a lower back injury, sending the American through to the quarter-finals.
Osaka, who was aiming for her fourth successive win after returning from maternity leave, had earlier caused Gauff plenty of problems as she took the opening set.
After a series of breaks to open the match, Osaka went into the changeover 3-2 up but received treatment on her back after appearing to struggle with her movement.
Some error-prone play by Gauff allowed Osaka to clinch a third break before serving out the opener, but she swiftly gave up a break to go behind in the second set.
Gauff ultimately edged a hard-fought, 51-minute second set featuring several more breaks, with Osaka retiring before the decider could get underway, having struggled to land her first serves in the latter stages.
Gauff now advances to the China Open quarter-finals for the second year in a row, with Ukraine's Yulia Starodubtsewa up next for the world number six.
Fellow American and second seed Jessica Pegula, meanwhile, was beaten in straight sets by Paula Badosa, who will face home favourite Zhang Shuai in the last eight.
Data Debrief: Twenty up for Gauff
The victory may not have come in the manner she envisaged, but Gauff has brought up her 20th career win over a former grand slam champion on the WTA Tour.
Since 2000, Gauff is the fifth player to achieve 20 such wins before turning 21, along with Maria Sharapova, Kim Clijsters (28 each), Martina Hingis (24) and Serena Williams (22).
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