Ben Shelton and Stefanos Tsitsipas will kick off their Shanghai campaigns when seeded players start taking the court on Friday. Shelton gets underway against Denis Shapovalov, while Tsitsipas faces Kei Nishikori.

(Q) Denis Shapovalov vs. (14) Ben Shelton

Shelton and Shapovalov will be going head-to-head for the third time in their careers and for the third time since the start of this summer when they meet again in round two of the Rolex Shanghai Masters on Friday. It’s safe to say that both of their first two encounters were memorable. Shelton prevailed in five sets at Wimbledon and then Shapovalov was defaulted for yelling at fan during a second-set tiebreaker in Washington, D.C. (Shelton was up triple-match point at the time).

The edge should go to Shelton once again, as he is in superior form right now and also loves playing in Asia. The 16th-ranked American captured the Tokyo title last fall and also upset Jannik Sinner at this same Shanghai tournament. Shapovalov already has three wins under his belt this week (two in qualifying and one over Lorenzo Sonego in a pair of tiebreakers), which could serve the 102nd-ranked Canadian well moving forward. Still, you have to like Shelton’s chances of picking up another win over Shapovalov.

Pick: Shelton in 3

(10) Stefanos Tsitsipas vs. (WC) Kei Nishikori

It has been a decent Asian swing so far for Nishikori, who is slowly making his way back to the top 100 in his latest tennis comeback (currently 153rd in the world). The Japanese veteran had to play Jerry Shang in the Chengdu opening round (Shang went on to capture the title), but he reached the Tokyo quarterfinals (lost to Holger Rune 7-5 in the third) and opened in Shanghai with a 3-6, 6-4, 6-3 victory over Mariano Navone.

Up next for Nishikori on Friday is a fourth contest against Tsitsipas, who trails the head-to-head series 2-1 after losing 6-4, 6-4 at the Montreal Masters this summer. That the 12th-ranked Greek should advance has little to do with his own level of tennis; he simply isn’t playing well at the moment. However, Nishikori was laboring at the end of his three-setter against Navone and making a quick recovery is not easy for a 34-year-old with an extensive history of injuries. Tsitsipas will probably be the beneficiary.

Pick: Tsitsipas in 2