Djokovic, who has won four of his 99 titles in Shanghai, next faces 61st-ranked Roman Safiullin who upset the 13th-seeded American Frances Tiafoe 5-7, 7-5, 7-6 (5). Stefanos Tsitsipas’ rivalry with Daniil Medvedev will add another chapter after the Greek player beat Alexandre Muller 6-3, 7-5.

Novak Djokovic, pursuing his 100th career title, moves on at the Shanghai Masters with a 6-1, 6-2 win over Flavio Cobolli on Tuesday.