World number three Alexander Zverev has fallen to 14th seed Denis Shapovalov, who moves through to a quarterfinal encounter with Rafael Nadal at the Australian Open.
Shapovalov defeated Zverev 6-3, 7-6 (7-5), 6-3 on Margaret Court Arena to earn his first last-eight berth at Melbourne Park.
Nadal won a first-set tiebreak lasting almost half an hour before going on to defeat France's Adrian Mannarino.
Nadal and Mannarino were level at 6-6 in the first set, with a tiebreak needed to snap the deadlock.
Both players had set points as the tiebreak wore on, with sixth-seeded Nadal eventually prevailing 16-14 after 28 minutes and 40 seconds.
The first set lasted more than 80 minutes, but Nadal found the going easier in the second and third sets as he powered his way to a 7-6 (16-14), 6-2, 6-2 victory in oppressive conditions on Rod Laver Arena.
It will be the Spaniard's 14th appearance in the quarterfinals at Melbourne Park. He won the 2009 title and was a runner-up in 2012, 2014, 2017 and 2019.
He is chasing a men's record 21st major singles championship.
The left-handed Shapovalov was magnificent against the German third seed, earning one of his biggest career victories.
He blew a match point with a wild forehand into the tramlines but wrapped up the contest when Zverev netted under pressure.
"Definitely happy with where the game is at," Shapovalov said in his on-court interview.
"I think off the ground I was just really playing very well, really feeling my shots off both wings."
Shapovalov said he was excited by the opportunity to face Nadal.
"It's always an honour to go up against a guy like Rafa," he said.
It was a disappointing exit for Zverev, who was bundled out of the quarterfinals by Novak Djokovic last year.
Late last year, Zverev suggested he and Russian Daniil Medvedev might become part of a new "big three" with world number one Djokovic in the 2022 season.
Meanwhile, Gael Monfils's blistering start to the season continued as he eased past Serbian Miomir Kecmanovic 7-5, 7-6 (7-4), 6-3 to reach his second Australian Open quarterfinal.
The French 17th seed next plays world number seven and Wimbledon runner-up Matteo Berrettini.
Italy's Berrettini progressed to the Australian Open quarterfinals for the first time in his career with a 7-5, 7-6 (7-4), 6-4 win over 19th-seeded Pablo Carreño Busta of Spain.
ABC/Reuters
