Novak Djokovic will enter the most important match of his illustrious career as a -260 favorite over Daniil Medvedev. They last faced in the 2021 Australian Open final where the Serb won handily, 7-5, 6-2, 6-2. Do not expect a repeat of that performance, as Medvedev plays his best tennis at the US Open, and Djokovic is sure to feel the weight of his Calendar Year Grand Slam pursuit as he closes in on the all-time major record in men’s tennis.

Both Djokovic and Medvedev have experienced momentary lapses in level throughout the fortnight, but have raised their game when they needed to. Medvedev dropping a set to Botic Van de Zandschulp in his quarterfinal round might have more to do with boredom than anything—he led the Dutchman 6-3, 6-0 before losing the third, 6-4.

Djokovic has dropped a set in his last four matches, most likely a function of his decision to skip the entire North American hard-court swing, opting instead to play his way into the tournament. Djokovic’s last four opponents—Holger Rune, Jenson Brooksby, Matteo Berrettini and Alexander Zverev—are also extremely dangerous in their own right. Locked at two sets apiece in Friday’s semifinal against a nearly flawless Zverev, Djokovic put the nail in the coffin when he raced to a 5-0 fifth set lead.

But Medvedev is one of the few opponents who can administer a taste of Djokovic's own medicine—routinely coming up with borderline impossible shots from every spot on the court.

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Djokovic employs the drop shot early and often, but against Medvedev, it had better be perfect. 

But Djokovic and his all-time great return cause major problems for Medvedev, who, in addition to his consistency and defense, relies heavily on free points won on serve. Djokovic will deny him that luxury, and force Medvedev to make tough decisions early on in the point.

How will Medvedev respond when Djokovic inevitably pastes a first-serve return within inches from the baseline?

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If you believe Medvedev will dethrone Djokovic, more power to you. But this one is easy for me. I will happily lose money backing the greatest men’s tennis player of all time to cover his -4.5 game spread in the most important match of his career. It’s like betting on Michael Jordan, Wayne Gretzky, Usain Bolt, Michael Phelps and Tom Brady: just go with greatness.

The Pick: Djokovic -4.5 games (-110) and -1.5 sets (-140)