Novak Djokovic reaches the fourth round of the Shanghai Masters

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

Djokovic grabbed his 19th winner, putting a forehand behind the Italian, who raced back over the baseline after being pushed wide by the serve.

The fourth-seeded Serbian did not allow a break point in the third round, having previously been stretched to two tiebreaks 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 13th-seeded American Frances Tiafoe 5-7, 7-5, 7-6 (5).

Stefanos Tsitsipas’ rivalry with Daniil Medvedev will add a new chapter after the Greek player defeated Alexandre Müller 6-3, 7-5.

The twelfth-ranked Tsitsipas and the Russian former US Open champion will meet for the fourteenth time, and for the first time in almost a year. Fifth-ranked Medvedev has a commanding 9-4 lead in the head-to-head series, which has led to a war of words off the field in the past.

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

Tsitsipas had to wait out a two-day rain break before playing his third-round match against Müller, but appeared to be in complete control until he lost his serve 5-3 in the second set. Unperturbed, the Greek broke back to love to win the match and renew his six-year rivalry with Medvedev.

No. 16 seed Ben Shelton dismissed 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 easily, beating Japan’s Yosuke Watanuki 6-3, 6-4, while Grigor Dimitrov, playing in his 100th Masters event, defeated 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 match. The 38-year-old Monfils, ranked 46th, is the second-oldest player to reach the fourth round in Shanghai, behind only Roger Federer (also 38) in 2019.

“It’s never easy playing against Ugo. He is very aggressive, plays fast from both wings and takes up a lot of your time,” said Monfils, who next plays Carlos Alcaraz at second.

Tomas Machac, who reached the semi-finals in Tokyo, also got past Australian Aleksandar Vukic 6-4, 6-2 and then faced No. 13 Tommy Paul in the third round.

Later Tuesday, third-seeded Alexander Zverev will face Tallon Greekpoor of the Netherlands in a night match.