Shanghai Masters semi-finals - Djokovic vs Vacherot and Rinderknech vs Medvedev, Previews and Betting Picks

The 2025 Shanghai Masters – one of the most bizarre tennis events in recent history – has just four men standing heading into its penultimate day. An already depleted draw suffered further upsets as cousins Arthur Rinderknech and Valentin Vacherot (image on top) continued their inspired runs. Can the pair go one step further and set the dream final in China? Read on for our 2025 Shanghai Masters semi-final preview and predictions.

Novak Djokovic vs Valentin Vacherot

Novak Djokovic standing in a Masters semi-final shouldn’t be a surprise to anyone. However, anyone that watched his matches will know that the Serbian getting this far is something of a miracle. Djokovic has faced down multiple health scares and some inspiring play from his opponents, besting Marin Cilic, Yannick Hanfmann, Jaume Munar and Zizou Bergs dropping two sets in total. All but the Cilic match were tough wins, with Djokovic battling a leg injury and general fatigue – including multiple on-court vomits – due to the brutal conditions in Shanghai this week.

His opponent world No 204 Valentin Vacherot is a massive surprise. The Monegasque player is playing the best tennis of his life, making a maiden Masters 1000 semi-final run that sees him rocket into the top 100 of the live rankings. Vacherot has found the somewhat slower conditions in Shanghai this year perfect for his hard hitting style and generally he’s been impeccable under pressure, coming back from a set down five times already this tournament.

His serve is massive, he is very capable from the baseline and he hasn’t dealt with the same problems related to heat probably due to having played in all sorts of conditions as a mostly challenger player. His path included wins over Nishesh Basavareddy and Liam Draxl in the qualifiers.

In the main draw he bested Laslo Djere, Alexander Bublik, Tomas Machac, Tallon Griekspoor and Holger Rune, dropping five sets in total to get here.

Djokovic vs Vacherot prediction

So who will win in this first matchup between the best player to ever grace a tennis court and a qualifier who is having the best week of his career? Anything but a Djokovic win naturally would be a massive shock, even with the troubles the four-time champion has had so far at the event.

Vacherot will certainly look to compete, but his issue is going to be a similar one to that which Bergs faced. When a rally developed, there was very little the Belgian could do. He either had to hit a winner or he was likely going to sail the bail wide trying to do that. We expect it will be the same with Vacherot.

So where does the value hide? We predict in our ATP Shanghai betting that Djokovic will be able to get the win fairly easily. Vacherot has played amazingly but when we look at the skillset and where he usually ranks, his fairytale has to end somewhere. Who better than merciless Djokovic – who will be eager to conserve energy heading into the final – to get it done. Let’s look at the best odds for this match.

Best bets on Djokovic vs Vacherot

Djokovic handicap games -4.5 @ 2.00 (+100)
Under 20.5 games @ 2.10 (+100)
Djokovic to win 2-0 @ 1.50 (-200)

Arthur Rinderknech vs Daniil Medvedev

Arthur Rinderknech is another player who wasn’t expected to be around at this stage of the Shanghai Masters. However, he has played amazing tennis to find himself in the semi-final. The serve is the story for the 6’5” Frenchman, as he’s been serving at an incredible rate, hitting aces 13% of the time across the event so far.

That has resulted in some impressive holding statistics as well as first serve winning percentages. He won 93% of first serves against Jiri Lehecka in the round of 16, and 85% against Felix Auger-Aliassime in the quarter-final. Beating a player who is holding serve that easily is a nightmare, especially on a surface which rewards good serves

To get to the semi-final, Rinderknech bested Hamad Medjedovic, Alex Michelsen, Alexander Zverev, Lehecka and Auger-Aliassime dropping only one set against that impressive list of players. That’s just how good he’s been as his level in many ways might have been the highest out of all players not named Daniil Medvedev and Djokovic.

His opponent will be the aforementioned Medvedev, who overcame his old nemesis Alex de Minaur to find himself in the semi-final. This event has been a reemergence of the Medvedev of old after the Russian struggled massively this season.

The Russian has simply been amazing, getting to every ball and counterpunching at an elite level. His serve has also been at a higher level than we’ve seen in 2025, which is a big deal as it has generated the kind of free points that Medvedev’s game is built around. His road to the semi-final included wins over Dalibor Svrcina, Alejandro Davidovich Fokina, Learner Tien and de Minaur.

He dropped only one set to get to the semi-final. However, it wasn’t an easy road as he nearly lost the Tien match. Medvedev remains shaky overall but this is the best he’s played in months. It’s not a surprise his form returned on these courts, as he won this event back in 2019 and has always enjoyed playing in Shanghai even though the conditions this year are much slower compared to what he usually likes.

Arthur Rinderknech vs Daniil Medvedev prediction

This is a very interesting matchup stylistically because on paper Medvedev should give Rinderknech a lot of trouble. Yet with how confident the Frenchman has looked, some might even view him as the favorite ahead of this matchup.

The key for Rinderknech will again be holding his serve in dominant fashion. Do so, and he may well be able to frustrate Medvedev enough for him to drift away from his game plan. When the Russian loses his head, things can fall apart and that’s not where he wants to be. Overall, this match projects to be a very closely contested clash that will likely see both players hold serve, so tiebreaks should be in store.

As for who will win, we’re liking Rinderknech because he’s largely looked unbothered by anybody he faced. Medvedev’s passive playstyle doesn’t seem likely to cause too much trouble either. The match is on the Frenchman’s racket. If he holds his nerve he will win, if not he won’t.