Novak Djokovic and Roger Federer have been knocked out at the quarter-final stage of the Rolex Shanghai Masters.
The world No 1 fell at the hands of Stefanos Tsitsipas, while Federer was defeated by Alexander Zverev on a dramatic day in China.
The conqueror of Djokovic, Tsitsipas, has struggled in recent months but found his form to produce a superb 3-6 7-5 6-3 victory – his second career win over Djokovic.
Djokovic sits at the top of the rankings at the moment but trails Rafa Nadal in the yearly standings and, with the Spaniard absent from Shanghai, had hoped to make up significant ground in China. “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.
“Stefanos had the high-quality tennis and he played very well after his serve,” the Serb added on the ATP Tour website.
“He was backing up his serve with really good and aggressive first shots in the rally. I didn’t make him defend enough. I just gave him enough time to really dictate the play from the back of the court and he deserved to win.”
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’ victory ensured he will make his debut at the ATP Finals in London next month.
Federer followed Djokovic out of the competition by losing a dramatic last eight clash 3-6 7-6 (7-5) 3-6 to Alexander Zverev.
Zverev, who has burst into life after a difficult season, missed five match points in the second set, with Federer finding some magic to recover from 40-0 at 6-5 and then saving two more match points in the tie-break.
There was more drama in the deciding set, with Federer quickly going down 3-0 and then engaging in a furious dialogue with the umpire after being given a rare point penalty for a hitting a ball into the stands for a second time.
Zverev managed to keep his cool and served out the victory at the second time of asking, taking his sixth match point. He will face either Matteo Berrettini or Dominic Thiem.