Wimbledon semifinal expert picks: Sinner vs. Djokovic

Expert picks are back for Friday’s second Wimbledon semifinal between Jannik Sinner and Novak Djokovic. The winner will battle either Alexander Zverev or Arthur Fery for the title. A three-team panel makes its predictions.

Ricky: Djokovic is way too big of an underdog in this matchup. He can never be discounted from any Grand Slam match, as he continues to excel on the big stage in the latter stages of his career. He also won his most recent meeting with Sinner in a five-setter in the 2026 Australian Open semis. And that’s why I think Friday’s showdown will be competitive — I don’t think Djokovic is going to pull off the outright upset. With two days off, the 39-year-old’s five-set marathon against Felix Auger-Aliassime should not be decisive factor moving forward. But it also certainly doesn’t help. Although Djokovic’s AO victory over the Italian was impressive, Sinner should not forget that had previously won five times in a row in their head-to-head series. He also should not forget that he is the best player in the world — by far. The top seed hasn’t played like it this fortnight, but he also wasn’t required to through his first five matches. I expect Djokovic to bring out the best in Sinner. Sinner in 4: 6-7(5), 6-3, 6-3, 6-4.

Cheryl: Sinner’s aura of invincibility was badly dented after his physical collapse in the second round of the French Open to Juan Manuel Cerundolo. He was a game away from an easy straight-set win when he suffered from an extreme reaction to the Paris heat. If it’s possible for a world No. 1 to quietly move through a draw, Sinner has done it. The Italian has gotten better with each passing round in London, but there seems to be this sense that he could just fall apart for no discernible reason again at any time. By contrast, the 39-year-old GOAT is still out there winning five-hour matches. His inspired performance against Auger-Aliassime was another chapter in the Stuff of Legends book he has been writing for two decades. Still, you have to wonder how his close to 40-year-old body is going to fare in the late stages of a grueling fortnight and a record-breaking match against FAA in the quarters. Djokovic nabbed Sinner somewhat unexpectedly at the Australian Open, but I have a hard time picking against the title favorite given how he is playing right now. Sinner in 5: 7-5, 4-6, 6-2, 3-6, 7-5.

Pete (Tennis Acumen): Nearly 35 years ago, 39-year-old Jimmy Connors reached the semifinals of the 1991 U.S. Open. At the time, as well as in the following decades, such an achievement seemed unlikely to be duplicated on the ATP Tour. Leave it to Djokovic to match the feat, currently at Wimbledon. Prior to the semifinals of the Australian Open earlier this year, Djokovic had not been able to solve Sinner’s game — he dropped 13 of the previous 15 sets they played in five matches heading into Melbourne. His come-from-behind five-set win there restored faith in his efforts against the Italian, but a five-hour victory in the quarters on Tuesday at the All-England Club will do his body no favors in this semi. Aside from a significantly more difficult-than-expected opening match against Miomir Kecmanovic that went the distance, Sinner has now won 14 consecutive sets — despite four of those going to tiebreakers. Djokovic is the first seeded player Sinner will face in London. The seven-time Wimbledon champion has won just a single one of his five matches in straight sets against significantly stronger competition. Full credit to Djokovic for reaching the semis, although his efforts in reaching this point of the tournament will be too much for him against the defending champ and current world No. 1. Sinner in 4: 6-3, 5-7, 6-3, 7-6(4).

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