The Pick, presented by DraftKings Sportsbook: Grigor Dimitrov vs. Denis Shapovalov, Cincinnati 

Two weeks ago, we won on a play in which we took Camila Osorio to defeat Sofia Kenin simply because the American just hadn’t shown an ability to win matches recently. Well, we’re going right back to that strategy by targeting world No. 22 Denis Shapovalov, who has now lost nine of his last 10 matches after defeating Rafael Nadal in Rome. The Canadian lost in straight sets against Alex de Minaur in Montreal, where you would have thought the home crowd would help him snap out of his funk. Now, we’re looking to 19th-ranked Grigor Dimitrov to defeat Shapovalov at the Western & Southern Open in Cincinnati.

Dimitrov also lost to De Minaur in Montreal, but he at least owns a winning record in 2022 and won this title five years ago. The Bulgarian is 20-16 on the year and his opponent in this match is 17-18. Dimitrov also has the better hard-court record between these two, as he is 246-157 on this surface in his career for a winning percentage of 61.0%. Meanwhile, Shapovalov only has a winning percentage of 56.0% on hard courts. And even if Dimitrov is just 2-2 in his last four matches, you' have to go back to May to find a second win for Shapovalov to throw on top of his victory over Arthur Rinderknech at Wimbledon.

It isn’t often that a player can be as mediocre as Dimitrov has been recently and still be the one that’s in better form than his opponent, but that’s where we find ourselves here. And perhaps Dimitrov will find some confidence in knowing just that. But outside of just the mental advantage the Bulgarian should have in this match, the 31-year-old also happens to have a rather large on-court edge here. This season, Dimitrov has a break percentage of 21.3%, which is a lower mark by his standards. However, that number is still a lot better than Shapovalov’s 15.3%. The 23-year-old just isn’t giving himself a chance to win matches because he isn’t reading serves well.

If Dimitrov is able to get a couple of breaks in this one, that can realistically be all there is to it. The Bulgarian is rock-solid with the ball on his own racquet, so he should have no trouble holding as long as he is staying focused throughout his service games. He’s also a smart enough player to know that he should be utilizing a good amount of spin when he can, as that will make it tough on the left-hander to comfortably hit his unorthodox backhand.

Finally, it’s also worth noting that Dimitrov is 2-0 in his two career hard-court matches against Shapovalov. Anybody that follows tennis knows that betting on the former world No. 3 can be a risky proposition, but it’s just hard to lay off of him in this spot.

The Pick: Dimitrov To Win (-120)