WTA Wimbledon second-round play begins on Wednesday. The top players advanced out of the first round, setting the stage for a second round that will have all the familiar big names on the schedule. 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
Sierra – Gauff: 6:00 EST
H2H: 0-2
This WTA Wimbledon tournament might be getting ready to bust loose in the second round, or it could stay calm. This match might give us an indication of what’s going to happen for most of the next 10 days. Coco Gauff has never been an especially good grass tennis player. She loves playing defense on clay, and she is very comfortable playing on hardcourts, having won the US Open championship. Grass has been different, because the surface plays a little faster and doesn’t have the same conditions as clay or hardcourts. Gauff entered this tournament seeded No. 7, her lowest seed at a major tournament in some time. However, she did look good in round one against Tamara Korpatsch. Is she ready to improve on grass? This match against Solana Sierra might give us a better feel for where Coco is.
Best Bet to Make
The price for Gauff winning in straight sets is small, so it’s definitely not worth betting on, especially since Gauff is not an elite grass tennis player. The right WTA Wimbledon betting play here is to go with the game spread. You could put Gauff minus 3.5 or 4.5 games into a parlay and see if you can cash multiple tickets, but the standalone wager should be Sierra plus 5.5 games. Sierra has won four grass matches this season compared to just one for Gauff. Coco leads the head-to-head 2-0, but the second match was a lot closer than the first, suggesting that Sierra felt more comfortable the more she saw of Gauff. Also, grass is not Coco’s preferred surface. This should be a reasonably close match, so Sierra plus the 5.5 games makes sense.
That being said, betting on Sierra +5.5 games is a value bet for sure.
Value bet/ the best odds: Sierra +5.5 games @1.96 @1xbet
Parry – Kalinskaya: Time 6:00 EST
H2H: 0-1
This is a really interesting WTA Wimbledon second-round matchup. Anna Kalinskaya is ranked No. 20, whereas Diane Parry is No. 49. Accordingly, Kalinskaya has been installed by the betting markets as a very clear favorite (1.55 moneyline). Yet, Parry has won five grass matches this season compared to just two for Kalinskaya. Parry loves playing on grass and feels at home on the surface. Kalinskaya has been inconsistent, though not terrible. It’s another scenario where the higher-ranked player is not the more in-form player. Is the gap in talent between the two players enough to trust the higher-ranked player, or is current form on the surface the more important factor for bettors?
Best Bet to Make
The pricing of this WTA Wimbledon match offers value to any pro-Parry bet. Parry plus 1.5 sets at 1.62 is something you should probably put into a parlay. You could also go for Kalinskaya moneyline in a parlay at the previously mentioned 1.55 price. However, while those are two good parlay pieces to consider, the ultimate recommended bet here is the over 2.5 set bet. Parry is in good form on grass, but Kalinskaya has considerable talent as a top-25 player. This is probably going to be a back-and-forth match in which each player has her good and bad moments. That’s generally what a three-set match looks like. The price, as always, can’t be beat.
That being said, betting on over 2.5 sets is a value bet for sure.
Value bet/ the best odds: over 2.5 sets @2.46 @betsson
Alexandrova – Tararudee: Time 6:00 EST
H2H: 0-0
Ekaterina Alexandrova struggled a lot on clay. She went through a very difficult period in her 2026 tennis season, during which she was losing more than she was winning. For a player who was ranked in the top 20, that was a very hard reality to deal with. When she got to grass, however, Alexandrova’s game and results improved. She wasn’t spectacular, but she was better. Alexandrova is 4-3 in seven grass matches played so far this season. Two of those losses were to players who have won multiple major tournament championships, Naomi Osaka and Aryna Sabalenka. So, the 4-3 record actually looks better than it is on paper. If Alexandrova had not played elite competition, she would probably have an even better grass record in 2026 as she enters this WTA Wimbledon second-round match.
Best Bet to Make
Lanlana Tararudee is ranked No. 99, 80 spots lower than Alexandrova, who is No. 19. With Alexandrova being in good form on grass and having won her first-round match in straight sets, there doesn’t seem to be a really good reason to bet against Alexandrova here. This should be a relatively straightforward win for the higher-ranked player. Alexandrova in straight sets doesn’t carry an amazing price, but it’s good enough for us to recommend it as our best bet.
That being said, betting on Alexandrova winning 2:0 is a value bet for sure.
Value bet/ the best odds: Alexandrova winning 2:0 @1.64 @1xbet
Main Photo Credit: Susan Mullane-USA TODAY Sports
