Pick of the Day: Novak Djokovic vs. Jannik Sinner, Shanghai

In the final of the Rolex Shanghai Masters, world No. 1 Jannik Sinner will take on 24-time Grand Slam champion Novak Djokovic for the first time since the Australian Open. Sinner won that match in convincing fashion, and the Italian ultimately went on to win his first major title. About six months later, after a loss to Carlos Alcaraz in the Wimbledon final, Djokovic specifically said that he’s not playing good enough tennis to beat the Spaniard or Sinner. However, we have seen flashes of greatness from the Serbian since, most notably in a win over Alcaraz in the gold medal match at the Paris Olympics. And I believe that Djokovic has what it takes to push Sinner here. That’s why I’m paying up a little to take Djokovic to win a set.

Sinner has played some great tennis throughout this tournament. The Italian has racked up five wins and only dropped a single set, which came against Tomas Martin Etcheverry. That’s especially impressive considering Sinner had to face Ben Shelton, Daniil Medvedev and a red-hot Tomas Machac. As he has all season, Sinner is serving and returning at a high level, and his baseline game has been impeccable. So Djokovic is going to have to bring his A-game in order to keep things close here. But I don’t see any reason to doubt the 37-year-old.

Djokovic has picked up some impressive wins of his own this week, including straight-setters over Flavio Cobolli and Taylor Fritz. Fritz, who has been playing at an insane level all throughout the hard-court season, played rather well in the match. But Djokovic was too much for him. The Serbian improved to 10-0 against the US Open runner-up, and that match should have Djokovic feeling somewhat prepared for Sinner.

Sinner is obviously a much better mover than Fritz, and the Italian has a more complete game. It’s really not even close. But it should help Djokovic that he just went up against a power server. Sinner is only marginally better than the American in that regard, and he hasn’t played anybody with Djokovic’s baseline ability in quite some time. Sure, Medvedev is a tremendous defensive player, but Djokovic is on a whole other level when it comes to turning defense into offense.

This is also a match that Djokovic is going to want badly. There are no Grand Slams left in the season, and this is an opportunity for him to add another 1000-level title—and prove that he is still firmly a part of this new Big Three. Djokovic is also going for the 100th title of his career, which is a serious milestone.

I’m not sure Djokovic will end up getting the job done in the end, but I definitely feel he has a good shot. And I’d be stunned if he doesn’t win at least one set.

Pick: Djokovic +1.5 Sets (-167)