Saturday is bringing some good matchups to the Shanghai Masters, here’s a preview for two of the clashes, Luciano Darderi vs. Stefanos Tsitsipas and Daniil Medvedev vs. Jan-Lennard Struff, with our predictions and best bets.
Luciano Darderi vs Stefanos Tsitsipas
Darderi, the 18th seed, gets his Shanghai campaign started off a first-round bye, and he arrives on the back of a mixed trip through Tokyo, where he opened with a 7-6(3), 6-3 win over Casper Ruud before falling to Kyrian Jacquet in the next round. It’s been a solid season for the Italian, who won the Chile Open in February, reached the Rome semifinal, where he beat Zverev after saving four match points, and hit a career-high No. 16 in May.
Tsitsipas has been rebuilding all year and climbed to No. 51 after his Gstaad title run in July, his first trophy of 2026. He started his week in Shanghai with a clean 6-3, 7-5 win over qualifier Kimmer Coppejans in the first round, so he’s got a match under his belt that Darderi doesn’t.
The two have met once before, in the first round of Halle in 2025, where Tsitsipas came through 6-4, 3-6, 7-6(5) in just over two hours.
Predictions and best bets
Two players that usually show their best game on clay. The seeding says Darderi is the favorite but the Greek enters as quite clear odds favorite on Saturday.
A difficult match to predict, especially with both players often showing inconsistencies but I think we will see 3 sets and it feels like Tsitsipas is the slightly better player on these hard-courts that are actually quite fast.
“I think it’s faster than Tokyo. I do feel the speed of the ball here” the Greek commented about the Shanghai courts.
My bet: Tsitsipas to win in three set, at odds 3.50 or +250.
Daniil Medvedev vs Jan-Lennard Struff
Medvedev, the 5th seed, comes in on the back of one of the strangest exits of the season. He had been cruising in Beijing, beating Pablo Carreno Busta 6-4, 6-2 and Struff 6-4, 6-3, before being disqualified from his semifinal against Djokovic after hitting a spectator with a ball. He loses the ranking points and prize money from that run, and he’s clinging to the final spot in the Nitto ATP Finals race with Djokovic and De Minaur closing in.
Struff, now 36 and ranked No. 59, opened his Shanghai campaign with a win over Martin Landaluce. His season hasn’t been consistent, 19-22 on the year, but he did get the better of Medvedev at Wimbledon back in July, before losing to him comfortably on hard in Beijing.
Medvedev leads the head-to-head 9-2, with both of Struff’s wins coming on grass, the most recent being the Wimbledon third round on July 3, 7-6(4), 7-6(5), 7-5. Medvedev won their last meeting on hard in Beijing last week.
Predictions
Struff’s wins over Medvedev have both come on grass, and the hard courts of Asia are a completely different story. Medvedev has dominated this matchup on this surface, and he has the added motivation of needing every ranking point he can get with the Finals race tightening. Despite the disqualification in Beijing, he’s looked solid and balanced lately and played some great tennis.
My bet: Medvedev to win in straight sets.
