Stefanos Tsitsipas and Alexander Zverev enjoyed landmark wins as Novak Djokovic and Roger Federer were both upset in the quarterfinals of the Shanghai Masters.
Federer and Djokovic had been a combined 13-0 in Shanghai with a spot in the semifinals on the line, but both lost Friday.
Federer saved five match points in the second set but still couldn’t stop fifth seed Zverev from winning 6-3 6-7 (7) 6-3.
Djokovic, the defending champion, lost to sixth seed Tsitsipas 3-6 7-5 6-3.
“He deserved the victory,” Djokovic said of the 21-year-old Tsitsipas.
“He was the better player in the second and third sets. I started well in the first set, but I wasn’t sharp enough.”
The winning moment for @AlexZverev from a great match.
His first top 10 victory of the season to secure back-to-back wins against @rogerfederer ????
— ATP Tour (@atptour) October 11, 2019
Djokovic had been 8-0 in quarterfinal matches at the Shanghai Masters, and won four titles. Federer had been 5-0.
Federer received a code violation for hitting a ball into the stands, and then received a point penalty for unsportsmanlike conduct after flicking a ball into the air when trailing 3-0 in the third set.
The 22-year-old Zverev now leads Federer 4-3 in career meetings, and goes on to face 11th seed Matteo Berrettini, who defeated fourth seed Dominic Thiem 7-6(8) 6-4.
Until Friday’s match, Djokovic had won 24 straight sets in Asia, a run that included last year’s Shanghai Masters and the title in Tokyo last week.
Tsitsipas has now beaten Djokovic twice in three matches.
The Greek player defeated Djokovic in their first meeting at the 2018 Toronto tournament and Djokovic won their match in Madrid this season.
“It’s the best comeback that I have ever had probably,” Tsitsipas said of Friday’s victory.
Tsitsipas also earned a place at the year-end ATP Finals for the first time on Friday. That was guaranteed when third seed T beat Fabio Fognini 6-3 7-6 (4) in another quarterfinal match.
Medvedev, who will face Tsitsipas in Saturday’s semifinals, is one match away from reaching a sixth consecutive tournament final.
He reached his first Grand Slam final at the US Open, and won titles in Cincinnati and St Petersburg.
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