This article is part of our Tennis Picks series.
Wimbledon begins Monday from the grass courts of the All England Lawn Tennis and Croquet Club in London with first-round play in both the gentlemen's and ladies' singles draws. Monday's action includes prominent matches featuring American women ranging from their teens to their 40s, as well as some value opportunities in matches featuring men's players who have made deep Wimbledon runs in previous years. All Tennis Odds & Lines are taken from DraftKings Sportsbook, but you can sometimes find more favorable odds on some of these matches by checking mobile sportsbooks such as FanDuel Sportsbook, BetMGM, Caesars Sportsbook, or any of the other best sports betting sites. We offer exclusive sign-up bonuses for some of those sportsbooks in states where sports betting has gone live, and Massachusetts was recently added to that list of eligible states.
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 considered overwhelming favorites, while the Value Bets section recommends enticing options in matchups that are considered closer to toss-ups.
Wimbledon Picks: Upset Alert
Sofia Kenin (+330) vs. Coco Gauff
Kenin has been unable to replicate the stellar level that helped her capture the 2020 Australian Open and ascend to No. 4 in the world, but the 24-year-old American has posted some encouraging results lately. She beat Aryna Sabalenka in Rome in May, and Kenin looked dominant in qualifying to earn a spot in the Wimbledon main draw. Kenin dropped three games or fewer in all six sets she played and notched an impressive win over compatriot Taylor Townsend in the final round of qualifying, so her elusive confidence may finally be returning. All the pressure will be on Gauff against the 128th-ranked Kenin in this match, and the world No. 7 has been up and down recently, notching multiple wins in only two of her last seven tournaments.
Diane Parry (+230) vs. Harriet Dart
Parry will have to overcome a hostile crowd against the British Dart, but the 20-year-old Frenchwoman is well positioned to pull this match out if she can do so. Parry has demonstrated impressive aptitude on grass in her young career. She reached the semifinals of junior Wimbledon in 2019 en route to capturing the world No. 1 junior ranking, and Parry made the third round here last year in her first professional Wimbledon appearance. At No. 96, Parry's also ranked 39 spots ahead of Dart, so while Dart has maintained a busy grass court schedule in England since the French Open, Parry's chances seem significantly understated at +230 odds.
Honorable Mentions
Jodie Burrage (+205) vs. Caty McNally, Stan Wawrinka (+180) vs. Emil Ruusuvuori
Wimbledon Odds: Lock It In
Elina Svitolina (-205) vs. Venus Williams
Williams getting to compete at Wimbledon again at age 43 via wild card is a nice story, but her last title here came 15 years ago, and the American is a shell of her former self on the tennis court, with a ranking outside the top 1,000. Svitolina's No. 76 ranking is deceiving, as she finished inside the top 15 every year between 2015 and 2022 but dropped in the rankings while sitting out during her pregnancy. The 28-year-old Ukrainian has picked up where she left off since returning to the tour, as Svitolina's coming off a quarterfinal result at the French Open.
Taylor Fritz (-425) vs. Yannick Hanfmann
Fritz is in the midst of another excellent season, as the world No. 9 is 33-14 in 2023. He pushed Rafael Nadal to a fifth-set tiebreak in the quarterfinals of last year's Wimbledon, and Fritz has his sights set on another deep run at the All England Club. The American's first-round match against the 48th-ranked Hanfmann should be relatively straightforward, as Hanfmann has only one win outside of clay this year and is 6-16 on other surfaces in his career.
Honorable Mention
Liudmila Samsonova (-290) vs. Ana Bogdan
Wimbledon Predictions: Value Bets
David Goffin (+120) vs. Nick Kyrgios
Kyrgios made the final here last year, but he has been limited to one match in 2023 by a knee injury -- a 7-5, 6-3 loss to Yibing Wu on June 13. The Aussie can serve his way out of trouble, but playing well on big points and closing out sets is especially tough after a lack of match play, and that's assuming that Kyrgios' knee is healthy enough to not drastically hamper his movement in this match. Goffin is as solid as they come, and while he's past his prime at age 32, the Belgian has made the quarterfinals in each of his last two Wimbledon appearances, including 2022. Goffin would have a fighting chance against a fully in-form Kyrgios here, and given the uncertainty over Kyrgios' health, Goffin's a nice value as the slight underdog.
Richard Gasquet (-185) vs. Corentin Moutet
Gasquet's one of the most accomplished grass court players on tour, as the 37-year-old Frenchman's 75-38 career record on the surface includes a pair of semifinal runs at Wimbledon. His countryman Moutet is just 3-6 on grass in his career, and Moutet's 2-7 overall in 2023. Gasquet also has a 31-spot edge in rankings at No. 49 in the world.
Honorable Mention
Yoshihito Nishioka (-140) vs. Daniel Elahi Galan
