This article is part of our Tennis Picks series.

The first round of Wimbledon begins Monday from the grass courts of the All England Club in London. A handful of women’s Grand Slam champions who have dropped outside the top 100 will get to work against higher-ranked opponents, while a top-10 seed on the men’s side could be headed for another early Wimbledon exit.

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.

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 overwhelming favorites, while the Value Bets section recommends enticing options in matchups that are considered closer to toss-ups.

Wimbledon Picks: Upset Alert

Alex Bolt (+225) vs. Casper Ruud

Ruud is a top-five player on clay and among the best on hard courts as well, but his game hasn’t meshed well with grass. The No. 8 seed is just 2-4 in his career at Wimbledon and hasn’t been past the second round. Bolt will be playing with house money here, as the 234th-ranked Australian went from getting into qualifying as an alternate to saving a match point in the final qualifying round just to make only his third career Wimbledon main draw. If Bolt’s name sounds familiar, it’s probably due to his near-victory over eventual finalist Dominic Thiem in the second round of the 2020 Australian Open, so Bolt has shown he can go toe-to-toe with a top player in a Grand Slam.

Diane Parry (+310) vs. Naomi Osaka

Osaka came the closest we have seen to replicating her pre-pregnancy level on the court in her second-round loss to Iga Swiatek at the French Open, but the four-time Grand Slam champion has gone just 2-2 since. She’s a pedestrian 15-12 overall in 2024 and ranked 113th, having failed to consistently find the timing necessary to execute her powerful, low-margin groundstrokes. Even when she was at her best, Osaka preferred hard courts to clay or grass, as she hasn’t been past the third round of the French Open or Wimbledon in her career. The 53rd-ranked Parry’s far from an easy first-round opponent, as the 21-year-old Frenchwoman has been to a Grand Slam third round on every surface in her young career and demonstrated her grass-court prowess by making the junior semifinals at Wimbledon in 2019.

Honorable Mention

Fabian Marozsan (+340) vs. Jan-Lennard Struff

Wimbledon Odds: Lock It In

Bianca Andreescu (-360) vs. Jaqueline Cristian

Andreescu has looked solid since returning from her most recent injury, posting a 6-3 record, including four grass-court wins to reach the final in ‘s-Hertogenbosch. The 2019 U.S. Open champion is a far better player than Cristian, who comes in with a career record of 2-6 in Grand Slam main draw matches. Andreescu is ranked 114 spots back of the 62nd-ranked Cristian, but as is true of a few big-name women on the comeback trail, that ranking is deceiving.

Zizou Bergs (-310) vs. Arthur Cazaux

Bergs is coming into his own at age 25. The late-blooming Belgian has played well across surfaces this year, climbing to a career-high No. 77 in the rankings earlier this month before dropping two spots. Bergs likes to get forward, making him a natural fit for grass. He has a nice first-round draw against Cazaux, who has dropped to 98th in the rankings after going 1-8 in his last nine matches, including a 1-3 mark against opponents outside the top 140.

Honorable Mention

Zhizhen Zhang (-500) vs. Maxime Janvier 

Wimbledon Predictions: Value Bets

Ekaterina Alexandrova (+105) vs. Emma Raducanu

Raducanu notched a grass-court win over Jessica Pegula in the lead-up to Wimbledon, but the 2021 U.S. Open champion has otherwise had an underwhelming run ever since that surprising triumph. Raducanu hasn’t been past the second round of a Grand Slam since and sits at 135th in the rankings. She’s better than her current ranking indicates, but it’s surprising to see Raducanu favored over the 22nd-ranked Alexandrova, who reached the Round of 16 at Wimbledon last year for the Russian’s best Grand Slam result. Even with the partisan crowd in Raducanu’s favor, the British star will be fighting an uphill battle against an opponent with significantly more power off the ground, making Alexandrova a nice value as the slight underdog. Alexandrova showed the heights she’s capable of reaching in Miami this year, beating Iga Swiatek and Pegula en route to the semifinals.

Christopher Eubanks (-110) vs. Quentin Halys

Eubanks has an ideal game for grass, as the lanky American’s 6-foot-7 frame helps him generate an impressive combination of power and angles on the serve while also aiding his reach at the net. He reached the quarterfinals at Wimbledon last year and has a 13-7 career record on grass compared to a 23-49 mark on other surfaces. Halys has dropped to 223rd in the rankings and has only two ATP Tour-level wins in 2024. The 27-year-old Frenchman has a 6-19 career Grand Slam main draw record.

Honorable Mention

Karolina Muchova (-110) vs. Paula Badosa