Wimbledon semifinal expert picks: Djokovic vs. Sinner, Alcaraz vs. Medvedev

Expert picks are back for the Wimbledon semifinals on Friday, when Novak Djokovic faces Jannik Sinner and Carlos Alcaraz does battle with Daniil Medvedev. A three-team panel previews the action and makes its predictions.

(8) Jannik Sinner vs. (2) Novak Djokovic

Ricky: This one of the few matchups involving Djokovic right now that are actually worth breaking down. Two of the others feature the two semifinalists on the other side of the Wimbledon draw, Carlos Alcaraz and Daniil Medvedev. It’s a blockbuster final four lineup at the All-England Club, and neither match on Friday should disappoint. Sinner is a heavy underdog, of course, but there are reasons to think he will be competitive. The eighth-ranked Italian led Djokovic two sets to love in the 2022 Wimbledon quarterfinals and he is a better, more experienced player one year later. Sinner is one of just a handful of guys on tour who have the firepower to–occasionally–take the racket out of Djokovic’s hands. Sustaining it over the course of a best-of-five match, however, is a different story. The 36-year-old Serb is supremely motivated, and when he’s motivated he is pretty much unbeatable. Count on his bid for the calendar-year Grand Slam to remain alive. Djokovic in 4: 6-4, 5-7, 6-3, 7-5.

Cheryl: Simply put, I won’t pick against Novak Djokovic at Wimbledon. He is a seven-time Wimbledon champion and holds the title from the last four times the event was held (there was no Championships in 2020 due to the Covid-19 pandemic). His mental toughness, his athleticism, and his innate understanding of how to win on grass are currently unmatched on the men’s tour. Still, it must be pointed out that Sinner had Djokovic on the ropes at last year’s Wimbledon. The young Italian was up two sets to none before Djokovic clawed his way back in their quarterfinal match. Sinner has only gotten stronger and more confident, so this semi should be a treat. Djokovic nearly always finds a way to win, and I expect that will be the case in this match, as well…but Sinner is going to make him work for it. Djokovic in 4: 5-7, 7-6(4), 7-5, 6-3

Pete (Tennis Acumen): Djokovic has had a significantly more difficult route to the semifinals, tested at the end by Stan Wawrinka, finding a way to ultimately break Hubert Hurkacz, and then dropping just eight games over the final three sets after dropping set one to Andrey Rublev in the quarterfinals. Sinner, meanwhile, has yet to face a seeded player. His path to the semis included wins over world No. 111 Juan Manuel Cerundolo, No. 98 Diego Schwartzman, No 79 Quentin Halys, No. 85 Daniel Elahi Galan, and No. 92 Roman Safiullin. Last year Djokovic ended Sinner’s run at Wimbledon in the quarters, coming from a two set to love deficit and surrendering only eight games in the final three sets to win the match. This match appears to be lopsided, tilted heavily in favor of Djokovic. That being said, Sinner proved that he can compete with the seven-time Wimbledon champion on Centre Court. While this would be quite the monumental win for Sinner, for Djokovic it is simply business as usual as he has his sights set on grander results this weekend and perhaps in New York later this summer. Djokovic in 4: 4-6, 6-3, 7-5, 6-4. 

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(1) Carlos Alcaraz vs. (3) Daniil Medvedev

Ricky: I had both of these semifinal matchups in my pre-tournament predictions (as did many!), and my pick for this one at the time was Alcaraz in four. I haven’t seen anything that changes my mind. Medvedev has been good, but Alcaraz has been great–at least toward the business end of the tournament. The top-ranked Spaniard was tested by Nicolas Jarry in the third round, but he mostly cruised against 2021 Wimbledon runner-up Matteo Berrettini in round four and then erased Holger Rune in easy straight sets to wrap up the quarterfinal schedule. If Alcaraz maintains that kind of level, he is going to be too good for Medvedev. The Russian, who is coming off a five-setter against Chris Eubanks, is a self-proclaimed hard-court specialist. I just can’t see him beating Alcaraz on any other surface at the moment. Alcaraz in 4: 6-7(5), 6-3, 7-5, 6-4.

Cheryl:  No. 1 vs. No. 3 in the semifinals of Wimbledon is the working definition of “not a surprise.” Except…it IS kind of a surprise. Perhaps not from Alcaraz, who works his way into the business end of almost every tournament he enters. But Medvedev had not exactly been impressive in his previous showings at the All-England Club. His best-ever result prior to this season was a fourth-round appearance in 2021. A grass-court expert he is not. Alcaraz gave Medvedev a shellacking when they met in the Indian Wells finals. This isn’t likely to be so one-sided; it will probably be more competitive. Still, the Spaniard has displayed impressive consistency. He has already won five titles in 2023, including the warm-up event at Queen’s Club. It’s hard to imagine Medvedev taking out Alcaraz when the top seed is in this form. Alcaraz in 4: 7-5, 4-6, 6-3, 7-5.

Pete: It has been quite the roller-coaster season this year for Medvedev, with a straight-set, third-round loss at the Australian Open, a 19-match winning streak ended by Alcaraz in the Indian Wells final, a pair of Masters 1000 titles in Miami and Rome, and a much earlier departure than expected in the opening round at Roland Garros. Since their meeting in the California desert in March, Alcaraz also won the Madrid Masters 1000 and breezed through an impressive field a few weeks ago at Queen’s Club. Both players had tussles in reaching the semis: Medvedev with Eubanks in the quarters, where he was a fourth-set tiebreak loss away from departing the tournament, and Alcaraz with Jarry and Berrettini in the third and fourth rounds, respectively. Sure they played here two years ago, Medvedev winning easily in straights; but Alcaraz was No. 75 in the world at the time and played a Challenger event two months prior. Where Medvedev would usually be able to find a way to win against most of the rest of the ATP field, he has few answers against Alcaraz in this semifinal. Alcaraz in 4: 6-3, 6-7(4), 7-5, 6-3.

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