Novak Djokovic's semifinal streak in Shanghai is over.
The defending champion from Serbia, a four-time winner of the Shanghai Masters who had reached the semifinals in all eight of his appearances at the tournament, lost to sixth-seeded Stefanos Tsitsipas 3-6, 7-5, 6-3 on Friday in the quarterfinals.
"He deserved the victory," Djokovic said. "He was the better player in the second and third sets. I started well in the first set, but I wasn't sharp enough."
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 21-year-old Greek defeated Djokovic in their first meeting at the 2018 Toronto tournament and Djokovic won their match in Madrid this season.
Tsitsipas also earned a place at the year-end ATP Finals for the first time on Friday. But that was guaranteed when third-seeded Daniil Medvedev 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 U.S. Open, and then won titles in Cincinnati and St. Petersburg.
Medvedev leads the tour with 57 match wins this season and is 40-1 on hard courts when winning the first set. The only time he lost a hard-court match after winning the first set was against Gael Monfils in Rotterdam.
Prior to Friday's match, Fognini said Medvedev was one of the most dangerous players to face.
"If some top players like Fabio can say this about me, shows that I'm on the good way, I'm playing good, and it's not easy to play against me," Medvedev said. "Surely, yeah, that's what I tried to show today on the match and it worked out."