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.

Pursuing a 100th career title, Novak Djokovic had an easier time in his second match at the Shanghai Masters in ousting Flavio Cobolli.

On Wednesday, Novak Djokovic (No. 4 in the world) takes on Roman Safiullin (No. 61) in the Round of 16 at the Rolex Shanghai Masters.Djokovic is the favorite (-752) to get to the quarterfinals