After a 7-5, 7-5 defeat to Dominic Thiem in his tournament opener, six-time champion Roger Federer may find it tricky to qualify for the last four of the ATP Finals.
The 32-year-old Serbian tennis star avenged his loss to the 21-year-old Greek 3 weeks earlier in the Shanghai Masters, with a 58-minute victory.
Meanwhile, world number one Novak Djokovic defeated Britain’s Kyle Edmund with 7-6(7) 6-1 to reach the Paris Masters quarter finals.
The 33-year-old Spanish left-hander moved one shy of Roger Federer's all-time men's record 20 Grand Slam triumphs and became the second-oldest New York champion in the Open era after Ken Rosewall in 1970 at age 35.
Grigor Dimitrov, 78th-ranked, delivered a stunning upset of Roger Federer in the US Open quarter-finals, fighting back for a 3-6, 6-4, 3-6, 6-4, 6-2 triumph over the Swiss star who had beaten him in all seven of their prior meetings.
Second seed Rafael Nadal – the winner at Flushing Meadows in 2010, 2013 and 2017 – produced some electrifying moments of brilliance to end the challenge of Croatia's Marin Cilic 6-3, 3-6, 6-1, 6-2.
World number two Rafael Nadal advanced to the US Open third round by walkover after Australian Thanasi Kokkinakis withdrew from the tournament with a right shoulder injury.
Osaka will face off against unseeded Pole Magda Linette, who she defeated earlier this year on her way to her second Grand Slam title at the Australian Open.
The most captivating modern rivalry in men's tennis returns to the scene of its most dramatic episode when Roger Federer and Rafael Nadal meet for a place in the Wimbledon final.
Federer and Nadal each won their quarter-finals to set up an epic semi-final between the two, whilst world number 1 Djokovic will face Bautista Agut for a place in the final.
Roger Federer, Novak Djokovic and Rafael Nadal eased into the Wimbledon quarter-finals as the sport's Grand Slam heavyweights continued to deliver blow after blow to their wilting lightweight rivals.
The 33-year-old Spaniard becomes the first player, man or woman, to win the same Slam 12 times after seeing off a brave challenge from a weary Thiem of Austria in a repeat of the 2018 final.
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