Wimbledon 2025: Seeded Americans Face Tough Draws Wednesday
Second-round play begins Wednesday at Wimbledon from the grass courts of the All England Club in London. A top-10 seed on the women's side is on upset alert after barely avoiding an upset in the first round, while a local favorite should give Londoners something to cheer about Wednesday.
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All men's singles matches at Grand Slams such as Wimbledon are best of five sets, while women's singles matches are best of three sets. A mix of players' previous grass court results, recent form and stylistic matchups can help pinpoint intriguing betting opportunities, both among favorites likely to cruise to victory and underdogs ready to pull off upsets. The aforementioned underdogs are highlighted in the Upset Alert section, the Lock It In section covers players who can safely be viewed as favorites, while the Value Bets section recommends enticing options in matchups that are considered closer to toss-ups.
Wimbledon Tennis Picks: Upset Alert
Olga Danilovic (+330) vs. Madison Keys
Danilovic is a bit of a late bloomer by tennis standards, but she's playing the best tennis of her career at age 24, having climbed into the top 40 while posting a 6-2 record in Grand Slam matches this year. Lefties are perennially tricky on grass with their ability to slice the serve out wide to the opposition's backhand, and Danilovic brings more power and athleticism to the table than many southpaws that rely more on craftiness. Keys' big hitting is effective on grass, but her signature kick serve loses a lot of its bite due to the lower bounce. The sixth-seeded American was broken five times in her narrow 6-7 (4), 7-5, 7-5 win over 58th-ranked Elena Gabriela Ruse, and the Australian Open champion could be staring down an early exit at Wimbledon if she doesn't raise her level here.
Jan-Lennard Struff (+210) vs. Felix Auger-Aliassime
Struff's variety-based game is much better suited for the natural surfaces, grass and clay, than hard courts. The 35-year-old German has made the third round or better three times apiece at Wimbledon and the French Open, including doing so at both last year, compared to just twice total at the Australian Open and U.S. Open combined. Auger-Aliassime has been plagued by inconsistency the past few years, as his attackable backhand puts pressure on his serve and forehand to be near-perfect and win points before opponents can exploit his weaker wing. The 25th-seeded Canadian had 26 aces but also 11 double faults in his ugly five-set first-round win over James Duckworth. FAA leads the head-to-head 3-2 over Struff, but this will be their first meeting on grass, and Struff won their only previous matchup on a surface other than hard court.
Honorable Mention
Viktoriya Tomova (+250) vs. Sonay Kartal
Wimbledon Tennis Odds: Lock It In
Katie Boulter (-425) vs. Solana Sierra
Boulter thrilled the British crowd with a 6-2, 3-6, 6-4 first-round win over No. 9 seed Paula Badosa, and the 43rd-ranked Englishwoman has an excellent chance to build on that big win in Round 2 against the 101st-ranked Sierra, who has spent most of her time playing low-level clay-court events. Boulter's big game is well-suited for grass, with two of her three career titles having come on this surface, while the 21-year-old Sierra will likely be battling some nerves in addition to a hostile crowd in the first Grand Slam second-round match of her career.
Donna Vekic (-380) vs. Cristina Bucsa
Vekic has had an underwhelming season in 2025, but the 2024 Wimbledon semifinalist looked impressive in her return to the All England Club, dismantling Kimberly Birrell 6-0, 6-4 in the first round. The Croatian's powerful baseline game has proven effective on all surfaces, while Bucsa has been a perennial easy out in Grand Slams. The 102nd-ranked Spaniard is just 8-14 in Grand Slam main draw matches, and the only time Bucsa advanced past the second round of a major was when she reached the third round of the 2023 Australian Open.
Honorable Mention
Elise Mertens (-450) vs. Ann Li
Wimbledon Tennis Predictions: Value Bets
Nicolas Jarry (-165) vs. Learner Tien
Jarry's riding high after coming back from two sets to love down to upset No. 8 seed Holger Rune in the first round. The 6-foot-7 Chilean served up 31 aces in that match, and his ability to win free points on serve consistently could be the difference against the 5-foot-11 Tien. Jarry has proven to be a tough out here in the past, pushing Carlos Alcaraz in a highly competitive four-setter in Wimbledon 2023. Tien capitalized on a favorable draw in his Wimbledon debut, beating fellow young American Nishesh Basavareddy in the first round, but the 19-year-old American's grass-court ability is still unproven. Jarry scored a 6-3, 6-4 grass-court win over Tien when they played in the qualifying of Halle just over two weeks ago.
Anastasia Pavlyuchenkova (+100) vs. Ashlyn Krueger
Experience goes a long way on grass given how small a portion of the season it makes up. Pavlyuchenkova has a significant edge in that department, as the 33-year-old Russian has been at least a quarterfinalist at each of the four Grand Slams, including Wimbledon back in 2016. She's in good grass-court form at the moment, making the semifinals of Eastbourne leading up to this tournament and knocking off two-time Wimbledon quarterfinalist Ajla Tomljanovic 4-6, 6-3, 6-2 in the first round. Krueger has a 19-spot edge in the rankings at No. 31, but the 21-year-old American is just 4-9 in Grand Slam main draw matches in her young career and has a 3-4 grass-court record in 2025, with all three wins coming against opponents ranked no higher than No. 275.
Honorable Mention
Jordan Thompson (+125) vs. Benjamin Bonzi
