WTA Eastbourne Round of 16 action unfolds on Wednesday. This is an important day for the players in Eastbourne. The winners will advance to the quarterfinals and thereby ensure they get three whole matches of play in this final week before Wimbledon. That would make this a good and productive week for them before they go to the All-England Club for the lawn tennis major championship of 2026. Losers of these matches might come to Wimbledon having not gotten as much experience or rhythm on grass as they probably would have liked. LWOS has our best bets for three matches. Post your best bets and thoughts in the comments.
WTA Eastbourne
Kessler – Kalinina: 7:30 EST
H2H: 0-0
McCartney Kessler and Anhelina Kalinina are separated by just eight spots in the WTA world rankings as they meet in the WTA Eastbourne tournament. Kessler is World No. 62, Kalinina No. 70. Kalinina has built her ranking over the course of 2026 and the first half of the year by going 30-8 in clay matches. Now she is transitioning to grass. It will be very interesting to see if she can beat a comparably ranked opponent on this surface. Kalinina playing 38 matches on clay represents a huge workload. Obviously, players who win matches play more matches. That’s how tennis works. Even then, 38 is a huge count, since the top professional players will usually focus only on Stuttgart or Linz, then Madrid, Rome, and Roland-Garros. Playing 38 matches means Kalinina has played a ton of clay tournaments. It adds to the uncertainty of how she will handle what’s left of the grass season. She has played only three grass matches, and Kessler (without nearly the same workload on clay) has also played just three grass matches this month.
Best Bet to Make
The tendency here for a grass tournament such as WTA Eastbourne is to lean to the player who hasn’t played 38 clay matches over the previous few months. That would be Kessler, due to doubts about Kalinina’s ability to handle the transition from clay (where she is very comfortable) to grass (where she is a lot less comfortable). However, Kessler has just one grass win this season. She might be physically fresher than Kalinina due to a much lighter match workload, but she hasn’t been especially strong when she has played. That doesn’t inspire confidence that she will actually win. This feels like a toss-up kind of match, and that’s exactly when you should bet over 2.5 sets. We use this bet a lot, and it doesn’t always hit, but we have seen it hit several times in recent weeks, and the payoff is absolutely fantastic when this bet cashes.
That being said, betting on over 2.5 sets is a value bet for sure.
Value bet/ the best odds: over 2.5 sets @2.40 @Betsson
Valentova – Tomljanovic: 7:30 EST
H2H: 0-0
Tereza Valentova found herself in a high-pressure situation. She played 17-year-old Hannah Klugman, a crowd favorite for the WTA Eastbourne crowd. She was pushed into a third set, and there was a hope that the British teenager would be able to pull off the upset. Valentova steadied herself and won a tough match. The big question is whether winning a close match like that will leave Valentova drained and weary, or will give her a lot of confidence and momentum going into this next match. Tomljanovic doesn’t figure to be an easy opponent, but maybe Valentova will ride a wave of confidence and become one of the big surprises at the WTA Eastbourne event.
Best Bet to Make
The reality here is that Tomljanovic really enjoys playing on grass. She is confident and comfortable on the surface. There’s a big gap in grass quality between the two players. Tomljanovic has six grass match victories this month, Valentova only one. Tomljanovic really struggled on clay earlier in the spring, but as soon as she got onto the grass this month, her game and results improved a lot. It’s hard to bet against Tomljanovic in this spot. The Tomljanovic moneyline price at WTA Eastbourne is generous. No need to bet on anything else here.
That being said, betting on Tomljanovic winning is a value bet for sure.
Value bet/ the best odds: Tomljanovic winning @1.73 @Bet365
Sonmez – Bejlek: 9:30 EST
H2H: 1-1
Sara Bejlek scored one of the wilder wins of the year in her recent WTA Eastbourne match against Laura Siegemund. Bejlek stumbled early, losing the first set 6-3 and immediately falling behind 2-0 in the second set. She looked done, or very close to it. Then she rallied and won three straight games. Siegemund asked for a medical timeout to check her vital signs. Bejlek led 5-3 in the second set but got broken. She had to work her way into a second-set tiebreaker to survive, and she won the tiebreaker. She and Siegemund then battled on even terms in the third set, fighting all the way to another tiebreaker. She won, capturing a victory which took over three hours to complete. People will wonder whether the result was due to Siegemund feeling physically unwell, but Bejlek still had to fight hard to win.
Best Bet to Make
This is the best WTA Eastbourne moneyline bet you can make for Wednesday and the Round of 16. Bejlek did very well to beat Siegemund. She had to fight really hard to win. However, she needed help from her opponent, and she still had to work more than three hours to win that match. Now she has to come right back against Sonmez, who beat Great Britain’s Harriet Dart and was able to win a match in front of a crowd that was cheering for her opponent. Bejlek is likely to be physically drained for this match. Sonmez should have more energy, and Sonmez won’t have a crowd rooting against her opponent. The price is not spectacular, but it’s decent, and the likelihood of the bet cashing on the WTA Eastbourne Wednesday card looks very high from what we can see.
That being said, betting on Sonmez winning is a value bet for sure.
Value bet/ the best odds: Sonmez winning @1.67 @Bet365
Main Photo Credit: Taya Gray-USA TODAY Sports
