Brandon Nakashima vs. Andrey Rublev

Nakashima has been rolling recently. The American has won 12 of his last 18 matches and is now up to 42-22 across all competitions in 2024. Nakashima is also coming off a massive win over Tommy Paul, moving to 3-0 in his head-to-head series with one of the top Americans in the sport. Nakashima has simply been healthy for most of the season, which is allowing him to play some of the best tennis of his life. Meanwhile, Rublev hasn’t exactly been great lately. The Russian has lost six of his last 11 matches, and some of those performances were truly awful. With that in mind, I like the American to take a set in this match. I’m also going to sprinkle the moneyline.

The reality here is that Nakashima is serving at an extremely high level. His hold percentage is up at 88.5% in 2024. That’s not going to make life any easier on Rublev. The Russian’s break percentage is way down this season, and that’s a big part of the reason he is losing matches.

Nakashima is also a level-headed player that is going to put his head down and focus on the task at hand. Rublev can run extremely hot and his temper has gotten the best of him this season. That’s pretty significant because I can see him getting a little frustrated as he attempts to break Nakashima’s booming serve.

Bet: Nakashima +1.5 Sets (-160 – 1.5 units) + Nakashima ML (+180 – 0.5 units)

Kei Nishikori vs. Nuno Borges

Nishikori was able to earn a shocking 6-4, 6-4 win over Stefanos Tsitsipas last round. That came directly after a 3-6, 7-5, 6-4 win over Alex Michelsen in the opening round. The 34-year-old is now being given a pretty good chance by the oddsmakers in his meeting with Borges. However, I think there’s a pretty significant gap between these two, which is why I’m putting a big play on the Portuguese player.

Nishikori might have been able to get the better of Tsitsipas, but that was a match in which the world No. 11 couldn’t stay out of his own way. Tsitsipas, who usually has one of the most dangerous forehands on tour, couldn’t get anything going on that side of the court. That’s a problem when you also consider Tsitsipas’ backhand is one of the weaker ones in tennis. So, while it was nice for Nishikori to earn a win over a top player, I’m not sure he deserves much credit. And Borges is going to be a lot tougher for him to beat.

Borges might not do much that stands out, but he’s a very solid server and he can be quite aggressive from the baseline. Borges takes the ball early and looks to move his opponents around the court. Both of those things should get to Nishikori here. I also just trust Borges’ fitness more here. Even if Nishikori comes out and takes a set, will he be able to maintain his level in the third? I have my doubts.

Overall, I just don’t view this version of Nishikori as a top-50 player, and I’m not even sure he’s a top-100 player at this point. That makes it hard not to love Borges, especially in conditions that suit him nicely.

Bet: Borges ML (-138 – 2 units)

Diana Shnaider vs. Coco Gauff

Shnaider has had some trouble getting to this point in the tournament. She barely squeaked by Harriet Dart in the first round, winning 6-3, 3-6, 7-6 (2). She then came away with a 2-6, 6-3, 7-6 (5) win over Magdalena Frech in the Round of 32. All in all, we haven’t seen a smooth transition from the Olympics to the hard courts in Toronto so far. However, Shnaider has the weapons required to make life difficult on Gauff, who didn’t look great in a 6-4, 6-4 win over Yafan Wang in her first match in Canada.

Gauff is obviously one of the most talented players in the world. She’s only 20 years old and has won a Grand Slam title. Nobody can take that away from her. However, Gauff’s forehand is still a serious problem, and she’s a little shaky as a server. Until those things change, she’s going to have her fair share of battles. And I can see this being one of them.

Rushing Gauff on the forehand side is one way to get the best of her, and Shnaider has the ability to do that. She is a very powerful player and she’s going to slap the ball to that side of the court. So, if the American isn’t avoiding mistakes and playing with shape, she could rack up errors in a hurry from the forehand wing. I also think that Shnaider’s ability to punish the ball will put a lot of pressure on the Gauff serve.

Shnaider has also just been playing some awesome tennis recently. She was one of the most impressive players throughout the grass-court season, she won a clay-court title in Budapest and she then won a silver medal in doubles at the Olympics. She should come to the court with a ton of confidence, and that will go far against this version of Gauff.

Bet: Shnaider +5.5 Games (-120 – 1.5 units)