Wimbledon semifinal expert picks: Sinner vs. Djokovic

Expert picks are back for the Wimbledon semifinal between Jannik Sinner and Novak Djokovic on Friday afternoon. A three-team panel offers analysis for the blockbuster matchup and makes its predictions.

Ricky: Sinner’s elbow may still be a small factor, but he looked a lot better in the quarterfinals against Ben Shelton than he did in the two sets against Grigor Dimitrov following his fall in the first game. With another full day of rest, the top seed might even be 100 percent for Friday. If he is even 90 percent, he should be able to beat Djokovic. After all, Sinner has won four in a row in the head-to-head series and five of their last six meetings. And each successive time they square off, Djokovic is getting farther and farther away from his prime and Sinner is getting closer and closer to his. That’s not to say the 38-year-old Serb can be discounted–especially not at Wimbledon, where he always either wins the title or at least makes it to the final. However, this version of Sinner is much different from the one Djokovic beat at the All-England Club in 2022 and 2023. The 23-year-old Italian has won the last two hard-court majors and there is no reason why he can’t win one on grass. Of course, he can worry about Carlos Alcaraz (probably) in the final later…after he beats Djokovic AGAIN. Sinner in 4: 7-6(5), 3-6, 6-3, 6-4.

Cheryl: Djokovic has been playing well this tournament. I bring this up because despite the fact that he continues to get to the business end of most events he enters, he has managed to do so without being at his best. But this fortnight his quality is some of the highest we have seen from him all season. The open question for the Serb is whether his “playing well” is good enough to take out the world No. 1. Sinner comes into Wimbledon off a crushing defeat at the hands of Alcaraz in the French Open final, a match in which he held three championship points that he failed to convert. But in true stoic Sinner style, he has shown no signs of mental fatigue. What he does have is the specter of an elbow injury hanging over him, sustained in his fourth-round match against Dimitrov. Sinner looked mortal in the Dimitrov match, down two sets to love before the Bulgarian retired due to a pectoral injury. Sinner was able to handle Shelton in straight sets on Wednesday–but he still looked human. I’m expecting Djokovic to have a better chance than he did in his straight-set trouncing at the hands of Sinner in Paris. And despite the fact that Djokovic is playing well and Sinner is a mortal right now, I can’t deny the fact that Sinner plays the Serb’s exact brand of tennis but does so on legs that are 15 years fresher. Sinner in 5: 7-5, 6-4, 4-6, 6-7(8), 6-3.

Pete (Tennis Acumen): Sinner has won the last four matches, including an astounding 10 of the last 12 sets played in this series. Quite a bit happened to flip the script in this H2H at the conclusion of 2023, as the Italian played Djokovic three times in less than two weeks and prevailed twice. They split the Nitto ATP Finals matches, Sinner winning in round-robin play and Djokovic claiming the championship match, and then Sinner then took their Davis Cup rubber a week later. Djokovic is appearing in his third consecutive major semifinal in 2025, while Sinner is attempting to reach the final in each of the slams played thus far this year. The top seed has to feel like he is playing with house money at this point after advancing to the quarters when Dimitrov was not able to continue their encounter despite leading by two sets. This will be the 18th major match played by Djokovic this year compared to just 17 in non-major tournaments. Clearly his emphasis and only priority are slams, and it certainly shows. Despite Miomir Kecmanovic declaring that his countryman can win 20 more slams the way he played in their third-round meeting, Djokovic is staring Father Time directly in the eyes and is taking one match at a time. The seven-time Wimbledon champion has been creating a significant number of break-point chances since the competition has intensified in his last few matches, and he is seeking to draw within one win of his 25th major title. Ironically, this will be the third time in the last four years they have played at Wimbledon, Djokovic winning both times. Sinner has yet to reach the final at the Championships…and he will need to wait a bit longer. Djokovic in 5: 6-7(4), 6-3, 6-4, 5-7, 6-4.