Novak Djokovic is on the quest for his 100th career title and had a straightforward victory in his second match at the Shanghai Masters, defeating Flavio Cobolli 6-1, 6-2 on Tuesday.

Djokovic secured the win with his 19th winner, executing a forehand shot just out of reach of the Italian, who was scrambling back across the baseline after being pushed wide by Djokovic's serve.

The fourth-seeded Serbian did not face any break points in this round, having previously endured two tiebreakers and saved set points against Alex Michelsen from the United States.

“Cobolli clearly seemed fatigued after his match last night,” Djokovic remarked about his opponent, who had advanced by defeating three-time Grand Slam champion Stan Wawrinka. “I believe that took a physical toll on him today.”

Djokovic, who has claimed four of his 99 titles in Shanghai, will next compete against 61st-ranked Roman Safiullin, who caused an upset by defeating Frances Tiafoe 5-7, 7-5, 7-6 (5).

After the match, Tiafoe congratulated Safiullin but left the court expressing frustration towards the umpire, who had issued a time violation just moments before on Tiafoe’s serve. It was unclear whether Tiafoe's action of tossing the ball was an attempt to serve.

Later on Tuesday, third-ranked Alexander Zverev also had a heated exchange with the umpire, using expletives after a correct call for a double bounce when he stretched to play a shot near the net.

Zverev ultimately converted his eighth match point to defeat Tallon Griekspoor 7-6 (6), 2-6, 7-6 (5).

In another match, Stefanos Tsitsipas continued his rivalry with Daniil Medvedev, defeating Alexandre Muller 6-3, 7-5.

The 12th-ranked Tsitsipas and the former U.S. Open champion Medvedev, currently ranked fifth, will face each other for the 14th time, marking their first encounter in nearly a year. Medvedev holds a significant 9-4 advantage in their head-to-head matchups, which have previously included off-court tensions.

“We’ve had some intense moments on the court before, but I believe those issues have settled over time,” Tsitsipas commented.

Tsitsipas endured a two-day rain delay before facing Muller in the third round, demonstrating strong control throughout the match until he dropped his serve at 5-3 in the second set. Remaining unfazed, the Greek player broke back without losing a point, securing the victory and reigniting his six-year rivalry with Medvedev.

Ben Shelton, ranked 16th, defeated Roberto Carballes Baena with a score of 6-3, 6-4, showcasing his power with eight aces and 24 winners, setting up a fourth-round clash with top seed Jannik Sinner.

Seventh-ranked Taylor Fritz also progressed smoothly, overcoming Japan’s Yosuke Watanuki 6-3, 6-4. Meanwhile, Grigor Dimitrov marked his 100th Masters event with a win against Alexei Popyrin, finishing 7-6 (5), 6-3.

In an all-French encounter, Gael Monfils pulled off an upset against 15th-ranked Ugo Humbert, winning 7-6 (7), 2-6, 6-1. At 38 years old and ranked 46th, Monfils is the second oldest player to reach the fourth round in Shanghai, following Roger Federer, who was also 38 in 2019.

“It’s always challenging to face Ugo; he plays aggressively and quickly from both sides, which can be quite disruptive,” Monfils remarked, as he prepares to take on second-ranked Carlos Alcaraz next.

Additionally, Tomas Machac, who reached the semifinals in Tokyo, comfortably defeated Australian Alexander Vukic 6-4, 6-2, and will next meet No. 13-ranked Tommy Paul in the third round.

At the Wuhan Open, Katerina Siniakova secured a straightforward 6-3, 6-1 win over Alexandra Eala from the Philippines, setting up a second-round match against defending champion Aryna Sabalenka.

Second-ranked Sabalenka, who claimed the title in 2019, needs to reach the quarterfinals in Wuhan to reclaim the top ranking from Iga Swiatek, who withdrew from the Asian swing due to fatigue and personal reasons. Swiatek has also recently parted ways with her coach, Tomasz Wiktorowski.

Poland's Magda Linette dominated No. 23-ranked Liudmila Samsonova with a score of 6-2, 6-2, while Ek.

Other notable winners were Katie Boulter from Britain, Amanda Anisimova from the United States, Viktoriya Tomova from Bulgaria, and Romania's Jaqueline Cristian, who is set to face Paris Olympics gold medalist Zheng Qinwen next.

After ending a 24-match losing streak at the China Open last week, Zhang Shuai's luck took a turn in Wuhan, where she was defeated by Kazakhstan's Yulia Putintseva with a score of 6-4, 6-4 in the opening round.

The top eight seeds, which include Sabalenka and China Open champion Coco Gauff, were granted a bye in the first round.