WTA Wimbledon first-round play begins on Monday. This is, for many, the crown jewel of all tennis tournaments, known locally as The Championships. The women’s tournament begins with Aryna Sabalenka and Elena Rybakina as the top two seeds, but they are not playing well and are not entering the All-England Club with much of any confidence. Iga Swiatek is the defending champion but is not playing well, either. There are a lot of questions in the women’s tournament, and there is a real chance the tournament will be as unpredictable as the French Open was a few weeks ago, with Mirra Andreeva playing Maja Chwalinska in a very unexpected final. What will happen at Wimbledon? There’s a lot of uncertainty, which should create a very exciting tournament. LWOS has our best bet for three matches. Post your best bets and thoughts in the comments.
WTA Wimbledon
Pegula – Vidmanova: 6:00 EST
H2H: 0-0
Jessica Pegula has a real chance to win this year’s WTA Wimbledon tournament. She made the final of the WTA 500 event in Berlin. In the process of getting to the final, she beat Aryna Sabalenka and Madison Keys. She is playing good tennis against quality competition. With Sabalenka struggling, Pegula has a chance to make a deep run. She is in the same half of the draw as Sabalenka, so she could potentially face the No. 1 seed in the semifinals if both players get there. Since Pegula recently defeated Sabalenka, she will enter that match with a lot of confidence, but first, she has to win five matches and get to the Wimbledon semis. Her first match is against Darja Vidmanova, who just won the WTA 125 outdoor hardcourt tournament in Portugal. Vidmanova played a small grass tournament earlier in the month at Ilkley. It will be interesting to see if the 125-point hardcourt tournament helped Vidmanova coming into Wimbledon on grass.
Best Bet to Make
There is real WTA Wimbledon intrigue surrounding Jessica Pegula’s bid for her first major championship. She has made one major final at the US Open but did not win it. This could be her best chance to win a major tournament. Roland-Garros was never going to be her main opportunity, since she is not as good on clay as she is on other surfaces. Pegula should certainly be able to handle Vidmanova in straight sets, but the price for a Pegula straight-set win is pretty low. You have to go with the game spread here. Pegula should not have a problem covering a 5.5-game spread. The price is not fantastic but the likelihood of winning is certainly very high.
That being said, betting on Pegula -5.5 games is a value bet for sure.
Value bet/ the best odds: Pegula -5.5 games @1.62 @Betway
Sawangkaew – Chwalinska: Time 6:00 EST
H2H: 0-0
This is one of the most fascinating first-round matches at WTA Wimbledon in 2026. On one side is Mananchaya Sawangkaew, who is ranked World No. 164. However, she has won seven grass matches this year and just won three Wimbledon qualifying matches at Roehampton. She is in good form and shows a reasonable amount of comfort on this surface. On the other side is Maja Chwalinska, who received a wild card from the All-England Club as a deserved reward for making the Roland-Garros final and pushing her world ranking from No. 114 to No. 21 in three weeks. Chwalinska almost became the second woman to win a major as a qualifier in the Open Era. The first was Emma Raducanu at the 2021 US Open. Chwalinska came one match short, losing to Mirra Andreeva in the final. She has not played a match since Roland-Garros. Who will win? The markets rightly have this priced as a virtual toss-up.
Best Bet to Make
This is a pick-a-winner match. Do you go with the lower-ranked player who shows real comfort on grass, or the much higher-ranked player who has built her ranking entirely on clay and has chosen not to play a single grass match this season? The answer seems clear: Pick the grass player. Chwalinska could have tried to play a grass warm-up tournament but didn’t want to. Sawangkaew played nine grass matches, winning seven of them. She qualified for WTA Wimbledon by winning three consecutive matches. If you take away Chwalinska’s Roland-Garros result, she would still be outside the top 100, and now she’s not playing on clay. Sawangkaew moneyline seems like the obvious choice at a great price.
That being said, betting on Sawangkaew winning is a value bet for sure.
Value bet/ the best odds: Sawangkaew winning @2.01 @1xBet
Li – Sonmez: Time 7:30 EST
H2H: 0-2
Ann Li is ranked No. 29. Zeynep Sonmez is ranked No. 54. Why is Sonmez the betting-market favorite for this WTA Wimbledon first-round match? It’s actually not that complicated. First of all, Sonmez is 2-0 head-to-head. Though that is not a huge sample size, one of the matches was earlier this year, making it fairly recent. The other big reason Sonmez is the betting-market favorite in this match even though she is ranked over 20 spots lower than Li is that she has won nine grass matches this season. Li has won only two. Sonmez shows real comfort on grass and enjoys playing on this surface. It’s up to Ann Li to turn the tables in this matchup, especially on grass.
Best Bet to Make
The benefit of the doubt goes to Sonmez because of her nine grass match victories this month. That shows a great comfort zone on the surface, and it’s hard to bet against that body of work when the opponent is not especially accomplished. It’s not as though Ann Li is a bad tennis player. She isn’t. Being a top-30 player is very solid. However, Zeynep Sonmez simply shows more potential on grass and has gotten better results. It’s hard to argue or bet against that. Sonmez moneyline is very generously priced, and that’s the best play to make here.
That being said, betting on Sonmez winning is a value bet for sure.
Value bet/ the best odds: Sonmez winning @1.80 @Pinnacle
Main Photo Credit: Mike Frey-USA TODAY Sports
