SHANGHAI - Canada's Denis Shapovalov and Felix Auger-Aliassime lost second-round singles matches Wednesday at the Shanghai Masters.
Shapovalov, from Richmond Hill, Ont., dropped a 6-3, 6-3 decision to top-ranked Novak Djokovic while sixth-seeded Stefanos Tsitsipas beat Auger-Aliassime 7-6 (3), 7-6 (3) for the Greek's first win in six attempts over the Montreal player.
The pair have met three times this season, with the other three games on the ITF junior circuit.
"Great. Very nice," said Tsitsipas, when asked how it felt to finally beat the 19th-ranked Auger-Aliassime. "I did things differently this time, but I prefer not to say what I did differently."
Djokovic, who had a bye into the second round, improved his career record against Shapovalov to 3-0 and has now won 22 straight sets in Asia — dating back to his title run in Shanghai last year and also including last week's Japan Open.
"Because of the history that I had in this tournament and in general in the Asian swing and lots of success and lots of matches won in my career, I actually feel less pressure because I'm more confident that I can perform at my best," Djokovic said.
The 36th-ranked Shapovalov struggled with his service game, hitting only 53 per cent of his first serves. Djokovic, who hit 74 per cent of his first serves, needed one hour 10 minutes to complete the victory.
In doubles play, Auger-Aliassime and Italy's Matteo Berrettini posted a 6-7 (4), 7-6 (5), 10-4 first-round victory over Croatia's Nikola Mektic and Franko Skugor.
Fifth-seeded Alexander Zverev advanced to the round of 16 with a 7-6 (13), 7-6 (3) win over French qualifier Jeremy Chardy. Zverev, who served 21 aces, saved three set points in the first-set tiebreaker. He won that tiebreaker on his sixth set point.
"It was a great tiebreaker obviously," Zverev said. "We both served incredibly well and didn't hit a lot of second serves ... Against Jeremy I always knew it was going to be tough especially on a surface like that, which is lightning fast. I think it's the fastest surface on tour."
His biggest problem in the second tiebreaker came when he lost his grip on his racket when hitting a forehand and watched it sail into the fourth row of the crowd. However, it landed in an empty seat and was quickly passed back down to the apologetic German.
Chardy has now lost 11 consecutive matches against top 10 opponents dating back to when he defeated then fourth-ranked Grigor Dimitrov of Bulgaria at the 2018 Miami Masters.
Dominic Thiem kept his momentum going after winning last week's China Open, beating Pablo Carreno Busta 7-6 (3), 6-3. Thiem had lost in the second round in Shanghai the last four years in a row.
The 16th-seeded John Isner was the only one of three Americans to advance, beating Lucas Pouille of France 7-5, 6-3.
Taylor Fritz fell to seventh-seeded Karen Khachanov of Russia 6-2, 6-4, and Reilly Opelka lost to eighth-seeded Robert Bautista Agut of Spain 6-4, 7-5.
With files from The Canadian Press.