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SHANGHAI — Pursuing a 100th career title, Novak Djokovic had an easier time in his second match at the Shanghai Masters in ousting Flavio Cobolli 6-1, 6-2 on Tuesday.

Djokovic clinched with his 19th winner, placing a forehand behind the Italian who was racing back across the baseline after being pushed wide by the service.

The fourth-seeded Serb did not allow a break point in the third round, after previously being stretched to two tiebreakers and saving set points against Alex Michelsen of the United States.

Djokovic, who has won four of his 99 titles in Shanghai, next faces 61st-ranked Roman Safiullin who upset the 13th-seeded American Frances Tiafoe 5-7, 7-5, 7-6 (5).

Stefanos Tsitsipas’ rivalry with Daniil Medvedev will add another chapter after the Greek player beat Alexandre Muller 6-3, 7-5.

The 12th-ranked Tsitsipas and the Russian former U.S. Open champion will meet for a 14th time, and first in nearly a year. The fifth-ranked Medvedev has a commanding 9-4 lead in the head-to-head series, which has spilled over into a war of words off the court in the past.

“I consider him someone that I respect on the tour, much more than I did before,” Tsitsipas said. “We’ve had some heated things on the court in the past, but I think those things have resolved themselves over time.”

Tsitsipas had to wait out a two-day rain delay to play his third-round match against Muller, but looked in complete control until losing his serve at 5-3 in the second set. Unperturbed, the Greek broke back to love to clinch the match and renew his six-year rivalry with Medvedev.

No. 16-ranked Ben Shelton put away Roberto Carballes Baena 6-3, 6-4, firing eight aces and 24 winners to line up top seed Jannik Sinner in the fourth round.

Seventh-ranked Taylor Fritz also advanced with ease, beating Japan’s Yosuke Watanuki 6-3, 6-4, while Grigor Dimitrov, playing in his 100th Masters event, beat Alexei Popyrin 7-6 (5), 6-3.

Gael Monfils upset 15th-ranked Ugo Humbert 7-6 (7), 2-6, 6-1 in an all-French matchup. The 38-year-old Monfils, ranked 46th, is the second oldest player to reach the Shanghai fourth round in Shanghai, behind only Roger Federer (also 38) in 2019.

“It’s never easy to play Ugo, he’s really aggressive, playing fast off both wings and takes a lot of time from you,” said Monfils, who plays second-ranked Carlos Alcaraz next.

Also, Tomas Machac, who made the semifinals in Tokyo, eased past Australian Alexander Vukic 6-4, 6-2 and next faces No. 13-ranked Tommy Paul in the third round.

Later Tuesday, third-ranked Alexander Zverev faces Tallon Griekspoor of the Netherlands in a night match.

Wuhan Open

Katerina Siniakova had a comfortable 6-3, 6-1 victory over Alexandra Eala of the Philippines to set up a second-round match against defending champion Aryna Sabalenka.

Second-ranked Sabalenka, who won the title the last time it was played in 2019, needs only to make the quarterfinals at Wuhan to regain top spot in the rankings from Iga Swiatek, who withdrew from the women’s Asian swing citing fatigue and personal reasons. Swiatek recently split with coach Tomasz Wiktorowski.

Magda Linette of Poland routed No. 23-ranked Liudmila Samsonova 6-2, 6-2, and Ekaterina Alexandrova beat former Australian Open champion Sofia Kenin of the U.S. 6-1, 4-6, 6-4.

Other winners included Britain’s Katie Boulter, American Amanda Anisimova, Bulgaria’s Viktoriya Tomova and Romania’s Jaqueline Cristian, who has Paris Olympics gold medallist Zheng Qinwen next,

After snapping a 24-match losing streak at the China Open last week, Zhang Shuai’s change of fortune turned in Wuhan as she lost to Yulia Putintseva of Kazakhstan 6-4, 6-4 in the first round.

The top eight seeds, including Sabalenka and China Open champion Coco Gauff, received a first-round bye.