WTA Wimbledon second-round play begins on Wednesday. The top players advanced out of the first round, setting the stage for a second round featuring all the familiar big names. Will this be a tournament in which the high seeds make it to the quarterfinals and semifinals, or will we see something like Roland-Garros, in which a lot of surprises and unexpected matchups emerged in the second week of the tournament? This second round might show what kind of path this event will take. Are we going to get stability and dependability, or will we see the kind of chaos that emerged in Paris four weeks ago? LWOS has our best bet for three matches. Post your best bets and thoughts in the comments.
WTA Wimbledon
Gasanova – Osaka: 6:00 EST
H2H: 0-0
The WTA Wimbledon second round begins on Wednesday with this battle involving four-time major champion Naomi Osaka. It is well known that Osaka struggles on grass. All four of her major titles are on hardcourts. Grass is a surface she has struggled to solve. In her first-round WTA Wimbledon match against Elsa Jacquemot, she easily won the first set but then fell behind 3-0 in the second set. She was able to regroup and rally to win the match in straight sets. She won, but her performance was far from flawless. Osaka has five grass match wins this year, largely due to making the Bad Homburg final. Gasanova has four match wins on grass this season, but she did not play the caliber of competition Osaka faced. Bad Homburg is a 500-point tournament, whereas Gasanova was playing much smaller events.
Best Bet to Make
The fact that Osaka has played stronger competition and has collected several grass match victories is important, but Osaka to win in straight sets is a bet with a low price. You have to go to the game spread. The evenly-priced spreads are 5.5 and 6.5 games. You could fold Osaka in straight sets and Osaka minus 5.5 games into a parlay, but for our standalone wager, we recommend Gasanova plus 6.5 games for a terrific price. Osaka will wobble on grass, as she showed against Jacquemot. Gasanova won’t win the match, or even one set, but she won’t completely get blown out.
That being said, betting on Gasanova +6.5 games is a value bet for sure.
Value bet/ the best odds: Gasanova +6.5 games @2.20 @bet365
Tjen – Kasatkina: Time 6:00 EST
H2H: 0-0
Janice Tjen and Daria Kasatkina enter their WTA Wimbledon second-round match having struggled recently. They are both 1-4 in their last five matches. Neither player has won more than two grass matches in this very short grass season. Tjen, however, opened some eyes by beating top-40 player Leylah Fernandez in the first round. It was a solid performance, though it should be added that Fernandez is also struggling and did not go into that match feeling good about her game. Kasatkina won the first set of her first-round match against Mimi Xu. She stumbled in the second set but then regrouped in the third to win. It was not a convincing performance, but enough to get the job done.
Best Bet to Make
When you have two struggling players and the markets have the match priced not that far from a toss-up (with some Kasatkina moneyline prices having her over 1.80 as a slight favorite), it’s not easy to pick an outright moneyline winner. If you can’t confidently and clearly pick a winner, that’s when you go to over 2.5 sets. Tjen is 1-4 in her last five matches, but the performance against Fernandez was good. Does that mean Tjen should be favored over Kasatkina? Maybe, but the markets don’t think so. You could wrestle with the moneyline play, but over 2.5 sets is a way of predicting a close match with neither player having to dominate for you to feel good about your bet. Over 2.5 sets is a way of saying this will be an inconsistent match, and that’s probably what this match will become.
That being said, betting on over 2.5 sets is a value bet for sure.
Value bet/ the best odds: over 2.5 sets @2.43 @betsson
Parks – Sawangkaew: Time 11:30 EST
H2H: 0-1
Mananchaya Sawangkaew got lucky in the first round of WTA Wimbledon, and so did we. We thought Sawangkaew would beat Maja Chwalinska because she had more grass match wins in 2026, and because we thought Chwalinska would struggle on grass after her big run at Roland-Garros. To be totally honest, Sawangkaew was not the better player at all. She lost the first set easily and then was down 5-2 and match point when Chwalinska got injured. Chwalinska needed medical attention. She obviously could not run very fluidly. She stayed on court for the rest of the match, but she was not the same player. Sawangkaew was able to outlast Chwalinska, but it was the injury, not anyone’s quality of play, which decided the match. Now Sawangkaew gets another chance to show she can play well at Wimbledon against Alycia Parks.
Best Bet to Make
The performance of Sawangkaew was very poor against Chwalinska. It’s very hard for us to feel confident about picking Sawangkaew in any way. This has to be a pro-Parks bet or a decision to fade Sawangkaew. Parks moneyline is reasonably priced. We don’t feel the need to make a bigger or more complicated bet.
That being said, betting on Parks winning is a value bet for sure.
Value bet/ the best odds: Parks winning @1.68 @pinnacle
Main Photo Credit: Mike Frey-USA TODAY Sports
