On Wednesday, Jannik Sinner (No. 1 in the world) meets Ben Shelton (No. 16) in the Round of 16 at the Rolex Shanghai Masters.Sinner is the favorite (-549) in this match compared to the underdog

Djokovic most recently played on August 30, 2024 in the Round of 32 of the US Open and was taken down 4-6, 4-6, 6-2, 4-6 by No. 28-ranked Alexei Popyrin. Over the past two years, Safiullin and Djokovic have played one time in the Round of 32 of the Rolex Monte-Carlo Masters, and Djokovic was the victor 6-1, 6-2.

Novak Djokovic of Serbia waves to spectators after defeating Flavio Cobolli of Italy in the men’s singles third round match of the Shanghai Masters tennis tournament at Qizhong Forest Sports City Tennis Center in Shanghai, China, Tuesday, Oct. 8, 2024. (AP Photo/Andy Wong)