For the sixth time in their careers and the second time this year, Jannik Sinner and Novak Djokovic will meet in the semifinal of a Grand Slam.

Sinner has won three of the five previous meetings at this juncture of a major, and the Italian is 6-5 overall against Djokovic, but the Serb won the most recent meeting at the Australian Open.

That result isn’t having much of an impact on the betting market, as Sinner is a chunky -465 favorite over Djokovic at FanDuel Sportsbook.

Wimbledon: Djokovic vs. Sinner odds, prediction

Neither player has been at their dominant best during the fortnight at Wimbledon. Sinner was taken to five sets right out of the gates by Miomir Kecmanovic, and he ended up on the right side of a couple of tiebreakers against Nuno Borges in Round 2.

He hasn’t dropped a set since his five-setter with Kecmanovic, but his only “routine” victories came against Jenson Brooksby and Shintaro Mochizuki. Even his straight-set triumph over Jan-Lennard Struff was more nervy than the scoreline suggested.


Jannik Sinner is searching for his second Wimbledon title. Best Image / BACKGRID

It’s nitpicky, but that’s what you have to be when handicapping Sinner. We’ve grown accustomed to the Italian steamrolling his way to Grand Slam finals. He hasn’t exactly done that at Wimbledon, plus he’s coming off that shocking wobble in the second round at Roland Garros.


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Djokovic’s journey to the semifinals has also been a roller coaster. The 24-time Grand Slam champion has only one straight-set victory, and he was pushed to the limit in the last round against Felix Auger-Aliassime. Djokovic’s 7-6, 3-6, 6-3, 6-7, 7-6 win was the longest quarterfinal match in the history of Wimbledon, spanning five hours and 14 minutes.

That’s a ton of time on court for the 39-year-old, but he catches a break with two full days off between then and Friday’s semifinal.

With neither player seemingly at the peak of their powers, I think we could see another classic as we saw in Melbourne when Djokovic won in five sets.

The pick: Djokovic to win 3-2 (10/1, FanDuel Sportsbook)


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Michael Leboff is a long-suffering Islanders fan, but a long-profiting sports bettor with 10 years of experience in the gambling industry. He loves using game theory to help punters win bracket pools, find long shots, and learn how to beat the market in mainstream and niche sports.



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