There are a couple of blockbuster matchups in the top quarter of the Shanghai draw on Wednesday, including Jannik Sinner vs. Ben Shelton. The winner will face either Daniil Medvedev or Stefanos Tsitsipas.

(1) Jannik Sinner vs. (14) Ben Shelton

Sinner and Shelton will be squaring off for the fifth time in their careers and for a second straight year in the Rolex Shanghai Masters round of 16 when they battle for a quarterfinal spot on Wednesday afternoon. Shelton won last year’s Shanghai showdown 2-6, 6-3, 7-6(5), but Sinner has since reeled off three victories in a row. The top-ranked Italian prevailed 7-6(2), 7-5 a couple of weeks later in Vienna, 7-6(4), 6-1 at the Indian Wells Masters in March, and 6-2, 6-4, 7-6(9) at Wimbledon this summer.

Although it has not been easy for Sinner at this tournament, it looks like he is motivated to keep his Asia winning streak alive. The 23-year-old triumphed in Beijing last week and so far in Shanghai has scraped past Taro Daniel 6-1, 6-4 and Tomas Martin Etcheverry 6-7(3), 6-4, 6-2. Shelton, who reached the Tokyo quarterfinals before falling to eventual champion Arthur Fils in a third-set tiebreaker, has rolled over Denis Shapovalov and Roberto Carballes Baena. This is a winnable match for the 16th-ranked American, but multiple days off following his struggle with Etcheverry should help Sinner–who is likely in line for another competitive victory in this matchup.

Pick: Sinner in 3

(10) Stefanos Tsitsipas vs. (5) Daniil Medvedev

One of the most entertaining rivalries in tennis will add another chapter when Medvedev and Tsitsipas meet for the 14th time in their careers. Medvedev leads the head-to-head series 9-4 after sweeping two matches last season–7-5, 7-5 in Rome and 6-4, 7-6(6) in Vienna. They previously faced each other in Shanghai five years ago, when Medvedev got the job done 7-6(5), 7-5.

It’s hard to see Tsitsipas turning the tide in his favor. The 26-year-old Greek has been mediocre this season, slumping to No. 12 in the rankings. He has advanced in Shanghai with defeats of Kei Nishikori and Alexandre Muller, although he was not particularly impressive in either contest. Medvedev has not yet captured in title in 2024, but he has been consistent. The fifth-ranked Russian’s bid for a second Shanghai title is off to a decent start with a straight-set success against Thiago Seyboth Wild and a three-set win over Matteo Arnaldi. Medvedev has not been happy with the balls at this event, but he has played well in the past when unhappy with certain conditions. Right now there probably aren’t any conditions in which Tsitsipas would beat Medvedev.

Pick: Medvedev in 2