Daniil Medvedev vs. Jannik Sinner

This head-to-head series has been one-way traffic recently. Sinner has won each of the last five meetings between these two, and the most recent was an absolute beatdown in Miami. However, it’s very difficult to win in straight sets against a good server on these courts. If Medvedev just hits his spots and stays solid on his own serve, he’s going to work his way deep into some sets and give himself chances to get on the board. It also doesn’t hurt that Sinner has been leaving the door open for his opponents in this tournament.

Sinner lost sets in his first two rounds, winning in four against both Yannick Hanfmann and Matteo Berrettini. He was also down a break and faced multiple set points in the third set against Ben Shelton last round. Well, Medvedev is a tougher opponent than all of those guys, and the Russian is essentially coming off a walkover against Grigor Dimitrov last round. The two didn’t even finish a full set before Dimitrov retired with a groin injury. That should mean that Medvedev will be rather fresh when he gets out there for this one.

This really just feels like a match that Sinner will win in four or five sets. His power and overall ability should win out in the end, but Medvedev is still a top-five player in the world. So, I can’t get on board with expecting Sinner to dust him — especially on a surface that suits Medvedev rather nicely.

Bet: Over 3.5 Sets (-167)

Tommy Paul vs. Carlos Alcaraz

I already have a future on Paul to win the quarter, so I need him to win this match. That said, I’m not personally playing this match. However, while I usually don’t like to give picks out for matches I’m already on, I felt the need to push myself to write something on this one. I just love Paul’s chances in this match, so I really think he’s worth a play on the game spread and a little moneyline sprinkle.

It’s just hard to ignore how bad Alcaraz has looked at this tournament. The defending Wimbledon champion and 2024 French Open winner nearly lost to Frances Tiafoe two matches ago. He then followed that performance up with a sloppy four-set win over Ugo Humbert. In that match, Alcaraz was looking at his box and telling them that he had no idea what to do against the Frenchman. The issue with Alcaraz right now is that his serve has gotten away from him a bit. And it’s hard to breeze through matches at Wimbledon without easily racking up holds. And that’s especially true when you’re facing a guy like Paul, who is one of the best returners on tour. Paul should give himself some chances to break here, and the American has also been serving well in Wimbledon.

Paul has also given Alcaraz a lot of trouble in the past, as he’s 2-2 against the Spaniard in his career. The most recent loss was a very tight battle in Cincinnati, which was also played in very fast conditions. It’s just not often that Alcaraz plays somebody that can come close to matching his athleticism, but Paul is pretty close in that regard. He’s one of the fastest players on tour, so he’s going to make Alcaraz play a lot of extra shots. That could lead to a high unforced error count. One of the reasons Alcaraz has been worse in 2024 than he was in 2023 is his shot selection, and this feels like a match in which he could make a lot of mistakes.

Bet: Paul +5.5 Games (-138 – 1.5 units) + Paul ML (+333 – 0.5 units)

Emma Navarro vs. Jasmine Paolini

I’m not thrilled about taking a play with this much juice, but I think Navarro is going to win and I want to have something on this. Navarro is 3-0 against Paolini in her career and there’s just not much that suggests that anything is bound to change in this head-to-head series. Paolini is one of the best competitors in the sport, and her will to win makes her an absolute backboard along the baseline. She also has the ability to hit for some power from the forehand side. But Navarro is also a player that gets a lot of balls back, and she’s just a little bit more powerful. So, she should be able to end rallies in a way that Paolini can’t. I also just trust Navarro a bit more as a server, and I think her ability to come to the net will be valuable in this match. Once she gets Paolini leaning in one direction or another, Navarro will come in and put points away.

I’m honestly just super high on the way that Navarro is playing. She went from a bit more of a grinder to a player with tremendous all-court ability. It no longer seems crazy to think that she’ll win majors some day, and I don’t even hate the idea of taking her to win this tournament.

Bet: Navarro ML (-185)