Sinner against Shelton, Medvedev against Tsitsipas

There are some blockbuster matchups in the top quarter of Wednesday's Shanghai draw, including Jannik Sinner versus Ben Shelton. The winner will face either Daniil Medvedev or Stefanos Tsitsipas.

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

Sinner and Shelton will face each other in the round of 16 of the Rolex Shanghai Masters for the fifth time in their careers and second consecutive year when they battle for a spot in the quarterfinals on Wednesday afternoon. Shelton won last year's showdown in Shanghai 2-6, 6-3, 7-6(5), but Sinner has rattled off three straight wins since then. The top-ranked Italian prevailed a few weeks later in Vienna with 7:6(2), 7:5, at the Indian Wells Masters in March with 7:6(4), 6:1 and 6:2, 6:4, 7-6(9) at Wimbledon this summer.

Although it wasn't easy for Sinner in this tournament, he seems motivated to continue his winning streak in Asia. The 23-year-old triumphed in Beijing last week and has so far beaten Taro Daniel 6:1, 6:4 and Tomas Martin Etcheverry 6:7(3), 6:4, 6:2 in Shanghai. Shelton, who reached the Tokyo quarterfinals before falling to eventual champion Arthur Fils in a third-set tiebreak, has overtaken Denis Shapovalov and Roberto Carballes Baena. This is a winnable game for the 16th-ranked American, but several days off after his battle with Etcheverry should help Sinner, who can likely pick up another competitive win in this clash.

Selection: Sinners 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 straight series 9-4, having won two games last season – 7-5, 7-5 in Rome and 6-4, 7-6(6) in Vienna. They already faced each other in Shanghai five years ago when Medvedev got the job done 7-6(5), 7-5.

It is hard to imagine that Tsitsipas could turn the tide in his favor. The 26-year-old Greek has been mediocre this season, plummeting to 12th place in the rankings. He continued to develop in Shanghai with wins over Kei Nishikori and Alexandre Muller, although he wasn't particularly impressive in either contest. Medvedev has not yet captured the title in 2024, but he has been consistent. The fifth-seeded Russian got off to a good start towards his second Shanghai title with a straight-sets win against Thiago Seyboth Wild and a three-set win against Matteo Arnaldi. Medvedev wasn't happy with the balls in this event, but he has played well in the past when he was unhappy with certain conditions. At the moment there are probably no conditions under which Tsitsipas would beat Medvedev.

Selection: Medvedev in 2