Jannik Sinner and Daniil Medvedev will be squaring off for the 14th time in their careers when they clash in the quarterfinals of the Rolex Shanghai Masters on Thursday.
Medvedev is leading the head-to-head series—and a very interesting one, too—by a 7-6 margin. The Russian won their first six encounters only to see Sinner reel off five victories in a row. Finally, they have actually alternated wins. Sinner has won three of their four meetings this season, but Medvedev pulled off a five-set upset at Wimbledon before the Italian got back on track with a four-set success at the U.S. Open.
Medvedev is obviously the underdog on Thursday, but he has to like his chances. The fifth seed is a former champion of this Masters 1000 tournament (2019) and is once again playing well in Shanghai with defeats of Thiago Seyboth Wild, Matteo Arnaldi, and Stefanos Tsitsipas.
Sinner dominated the fall swing in 2023 and is undefeated so far in Asia. The world No. 1 lifted the trophy in Beijing before kicking off his Shanghai campaign with victories over Taro Daniel, Tomas Martin Etcheverry, and Ben Shelton. However, Sinner was far from dominant in Beijing has looked somewhat vulnerable in Shanghai—especially against Etcheverry. The 23-year-old has been put through the ringer physically and mentally in 2024, so it only makes sense if he is not quite 100 percent for the stretch run.
So far at this event, Medvedev has complained about the quality of the balls and has dealt with a minor shoulder issue (took a medical timeout following the first set against Tsitsipas). The world No. 5 is one of those guys who seems to play better when there are certain factors working against him. That has been the case so far in Shanghai and it very well could continue.
Pick: Medvedev in 3
