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Novak Djokovic and Jannik Sinner at Wimbledon.

ATP Wimbledon Round of 16 Best Bets Including Jannik Sinner vs Shintaro Mochizuki

ATP Wimbledon Round of 16 play begins on Sunday. I have some bad news: Dave Barasic is no longer with us. I’ll try to cover some of his load while we hire a replacement. I want to thank those of you who sent me an email about my picks, as we aim to make you guys happy. With all of that out of the way,  LWOS has our best bet for four matches. Post your best bets and thoughts in the comments.

ATP Wimbledon

Hurkacz – Struff: 6:00 EST

H2H: 2-2

This is a very interesting ATP Wimbledon Round of 16 match between two big hitters who have generally underachieved. Hubert Hurkacz and Jan-Lennard Struff can both look great at times but are known for being inconsistent players who can’t remain steady. Both are having a strong ATP Wimbledon showing, however. Hurkacz has made his way through Casper Ruud, solid grass tennis player Sebastian Ofner, and always-dangerous American Tommy Paul. That’s a really good set of wins. Struff trailed Brandon Nakashima late in the fifth set but rallied to win. He then knocked out Daniil Medvedev in a very impressive performance. These are in-form players battling for a spot in the quarterfinals. Who will come out on top?

Best Bet to Make

Struff is obviously playing with confidence, but he was a break down in both the second and third sets of his win over Medvedev in the third round. He didn’t dominate as much as the final score might have indicated. He was fortunate to get past Nakashima in the previous round, too. He easily could have lost that match. Hurkacz has been a little more solid and consistent in this tournament compared to Struff. Hurkacz has made the Wimbledon semifinals before. When he gets comfortable on grass, he becomes very hard to beat. Hurkacz in four sets looks just about right here. That’s our play: Hurkacz minus 1.5 sets.

That being said, betting on Hurkacz -1.5 sets is a value bet for sure.

Value bet/ the best odds: Hurkacz -1.5 sets @1.67 @betway

Safiullin – Djokovic: 8:30 EST

H2H: 0-3

Novak Djokovic is trying to get back to the ATP Wimbledon semifinals, where he could possibly face Jannik Sinner. He needs two more wins to reach the semifinals. This match against Roman Safiullin will be eagerly anticipated. Djokovic has looked good but not great in his first few match wins. He had some wobbles against Yibing Wu in the first round and nearly got taken to a fifth set by Arthur Rinderknech in the third round. He played a smooth match against Stefanos Tsitsipas in the second round, but that’s a matchup which has worked well for him in the past. Safiullin is coming off his best performance of 2026, a three-set win over Joao Fonseca. If he plays like that against Djokovic, this match will be a long one, but can Safiullin actually do that? It’s the question for bettors to weigh. 

Best Bet to Make

Safiullin can make this match really interesting, but it’s very hard to expect him to play three whole sets as well as he played against Fonseca. The best way to handle this match as a bettor is to make one bet on each side. Djokovic minus 4.5 games can be a parlay piece at 1.56, but then Safiullin to win one set (plus 2.5 sets) comes in at 1.60. You could maybe sprinkle a little extra on Djokovic minus 5.5 games at the better price, but the main point is to have Djokovic on the game spread and Safiullin on the set spread. You can cash two tickets if it falls just right. Our official play, since the price is better, is Safiullin on the set spread.

That being said, betting on Safiullin +2.5 sets is a value bet for sure.

Value bet/ the best odds: Safiullin +2.5 sets @1.60 @10bet

Jul 13, 2025; Wimbledon, United Kingdom; Jannik Sinner (ITA) stands on the South West Hall balcony holding the gentlemen's singles champion trophy, after his match against Carlos Alcaraz (ESP)(not pictured) in the gentlemen's' singles final of The Champi… | Source: Lastwordonsports.com - Shane Black

Auger Aliassime – Davidovich Fokina: Time 9:30 EST

H2H: 5-1

This is a big opportunity for both players to get to the ATP Wimbledon quarterfinals and see if they can challenge for the championship as the week continues. Felix Auger Aliassime and Alejandro Davidovich Fokina both looked really good in their first three rounds. They both won nine sets out of nine. They have not lost a set. Now they meet. Will they both maintain the good form they have shown or will one player lose focus? The pressure of the situation, with a quarterfinal spot on the line, could affect how one or both players play. It’s going to be a challenge for them to maintain composure. It’s part of what makes this match interesting.

Best Bet to Make

The fact that Auger Aliassime is 5-1 in the head-to-head matchup is hard to overlook here. There’s something in Davidovich Fokina’s game that Felix finds comfortable to play against. Therefore, the bets made on this match should be pro-Auger Aliassime. You could go with the set spread for a better price. Minus 1.5 sets is definitely worth considering. However, in a best-of-five-set men’s match, game spread is generally better than set spread because a match can go five sets and yet the winning player will usually (not always) collect enough games to win your bet. Felix minus 2.5 games is a very small spread, but you’re getting a good price for that. Felix moneyline is 1.52, but minus 2.5 games is noticeably better than that. Chances are if Felix wins the match, he will also be minus 2.5 games, so that’s the best play to make, more than a set spread bet.

That being said, betting on Auger Aliassime -2.5 games is a value bet for sure.

Value bet/ the best odds: Auger Aliassime -2.5 games @1.73 @bet-at-home

Sinner – Mochizuki: Time 12:00 EST

H2H: 0-0

Jannik Sinner continues his pursuit of another ATP Wimbledon title when he takes the court in the Round of 16 against Shintaro Mochizuki. Sinner struggled for parts of his first two matches at the All-England Club, but he looked better in the third round against Jenson Brooksby, winning in straight sets. Sinner needed five sets in his first-round match, and he wobbled in the first two sets of his second-round match, but he was sharper against Brooksby and hopes to carry that kind of form into the Round of 16. Mochizuki opened some eyes by knocking off rising Spanish youngster Rafael Jodar in the third round. Mochizuki didn’t dominate the match but was able to respond really well whenever Jodar challenged him. Now Mochizuki faces an even bigger test. It will be interesting to see what he can do.

Best Bet to Make

Sinner’s improvement in the Brooksby match makes it easy to think he will win this match in straight sets. However, Sinner winning in straight sets is not priced very highly. You won’t get real value there. So, you have to go to the game spread bet in this situation. The evenly-priced game spreads are 9.5 and 10.5 games. You could put Sinner in straight sets and Sinner minus 7.5 or 8.5 games into multiple parlays so that you have a Sinner ticket to work with. However, for our standalone bet, we think Mochizuki plus 9.5 games is the right play. Mochizuki is obviously playing great tennis. At a 9.5-game spread, he could lose 6-3, 6-3, 6-3 and still cash a winning ticket. The spread seems just a little high for Sinner, though he could clearly cover it. This is why you should have some Sinner parlays involved. Mochizuki against the game spread, though, is our best bet. 

That being said, betting on Mochizuki +9.5 games is a value bet for sure.

Value bet/ the best odds: Mochizuki +9.5 games @1.93 @1xbet

Main Photo Credit: Susan Mullane-USA TODAY Sports