The Greek former world No. 3 produced a composed performance against the 18th-seeded Italian, advancing at the ATP Masters 1000 tournament and reaching the third round for the third time this season.
Tsitsipas reaches landmark 400th win
Tsitsipas became the ninth active men's player to reach 400 tour-level victories, joining an elite group that includes Novak Djokovic, Alexander Zverev, Daniil Medvedev and Andrey Rublev.
The milestone came nine years after he recorded his first tour-level victory in Shanghai in 2017, when he defeated Karen Khachanov in the opening round.
Since then, the 28-year-old has established himself among the leading players of his generation, collecting 13 tour-level titles, including the 2019 Nitto ATP Finals crown, and reaching a career-high ranking of world No. 3.
According to the ATP Tour's statistics, Tsitsipas entered the milestone with a career record of 400 wins and 204 defeats.
Greek overcomes Darderi in straight sets
Tsitsipas controlled the contest to defeat Darderi 6–3, 6–4 and secure his place in the last 32.
The victory continued his progress in Shanghai after an opening-round win over Belgian qualifier Kimmer Coppejans, whom he defeated 6–3, 7–5.
The Greek will now face American Taylor Fritz, the 11th seed, in the third round. Fritz advanced after beating Italy's Matteo Arnaldi 7–5, 6–4.
Fritz challenge awaits in the third round
The upcoming meeting presents Tsitsipas with an opportunity to build on his momentum and make a deeper run in Shanghai.
Fritz, a former semi-finalist at the tournament, is also pursuing valuable ranking points as the season approaches its conclusion and the race to qualify for the Nitto ATP Finals intensifies.
Tsitsipas will need another disciplined performance against the American if he is to progress to the fourth round.
For the Greek, however, the victory over Darderi has already provided a memorable milestone in a career that continues to add to his place among the ATP Tour's leading active players.