Seeds Taylor Fritz and Arthur Fils will try to secure their spots in the Shanghai Masters fourth round on Monday. They are going up against Stefanos Tsitsipas and Botic van de Zandschulp, respectively.

Stefanos Tsitsipas vs. (11) Taylor Fritz
Fritz and Tsitsipas will be squaring off for the seventh time in their careers when they clash in round three of the Rolex Shanghai Masters on Monday. Tsitsipas leads the head-to-head series 4-2, although they have split their four outdoor hard-court contests at two wins apiece. Fritz won each of their last two meetings in regular tournament competition before Tsitsipas scored a 6-4, 7-5 victory at the United Cup earlier this season.

The 28-year-old Greek has found his game following a rough start to the 2026 campaign, enjoying a second-half stretch that features a title in Gstaad and a fourth-round performance in New York. He advanced to the Tokyo second round last week as a qualifier and so far in Shanghai has dismissed Kimmer Coppejans and Luciano Darderi in straight sets. Fritz, who defeated Matteo Arnaldi 7-5, 6-4 on Saturday, needs to make a late push for Nitto ATP Finals contention. The 12th-ranked American is currently 12th in the race. A motivated Fritz should have a slight edge over Tsitsipas on a relatively fast hard court.

Pick: Fritz in 3

(8) Arthur Fils vs. Botic van de Zandschulp
Fils also has his eyes on the Nitto ATP Finals and is in great shape to make his Turin debut. The 22-year-old Frenchman is No. 7 in the live race and that effectively puts him in the sixth spot since Jannik Sinner is out for the season. Fils lost right away at the U.S. Open to Tsitsipas but rebounded to reach to the Tokyo quarterfinals with a win over Tiafoe, and he opened in Shanghai by beating Pavel Kotov 6-3, 6-4.

Up next for the Cincinnati champion is a second encounter with Van de Zandschulp, who lost their only previous matchup 6-2, 4-6, 6-1 on the red clay of the 2024 Bordeaux Challenger. The 41st-ranked Dutchman made a run to the quarterfinals at Flushing Meadows, but his Asian swing has been a mixed bag so far. He failed to win a main-draw match in either Chengdu or Beijing before advancing in Shanghai with defeats of Daniel Merida and Alex Michelsen. Van de Zandschulp’s ceiling is high, but his floor is much lower than that of Fils. It may be too much to ask of the underdog to string together a third consecutive great match, and Fils is eager to punch his Turin ticket.

Pick: Fils in 2