Eight and a half years ago in Miami, a 22-year-old Daniil Medvedev and a 19-year-old Stefanos Tsitsipas, both outside the top 50, played a first-round match that ended with the Russian shouting at the Greek from his bench.
Daniil Medvedev and Stefanos Tsitsipas will face each other for the 16th time in the round of 16 at the Shanghai Masters. Medvedev enters as the No. 5 seed and leads their career head-to-head record 10-5. However, Tsitsipas won their most recent meeting in straight sets in Doha in February 2026.
The matchup marks another chapter in a long-standing rivalry that began in 2018 with significant tension before evolving into a more respectful dynamic. Both competitors arrive in Shanghai following eventful weeks, with Medvedev recently winning Hangzhou before suffering a default in Beijing, while Tsitsipas earned his 400th career victory and defeated Taylor Fritz.
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