This article is part of our Tennis Picks series.
Thursday at Wimbledon will include both first-round and second-round matches as we continue to chip away at the backlog created by inclement weather over the first few days of tennis from the grass courts at the All England Lawn Tennis and Croquet Club in London. A couple of Canadians at far different points in their respective careers will both be hunting upsets, while a pair of surprising slight underdogs should provide good value against opponents they have proven capable of beating before. 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
Milos Raonic (+200) vs. Tommy Paul
Raonic missed two years due to injuries, but the 2016 Wimbledon finalist has a game tailor-made for grass, with a booming serve and plenty of power off the ground. Paul's one of the best returners in the game, but Raonic is capable of taking the racquet out of his opponent's hands with his serve, and since this tournament may well be part of his farewell tour, the Canadian won't be feeling as much pressure on big points as the 15th-ranked American. If Raonic's body can hold up playing on back-to-back days, he has the game to pull off the upset here.
Leylah Fernandez (+200) vs. Caroline Garcia
These two have seen plenty of each other this year, as Garcia beat Fernandez 7-6 (5), 7-5 at the Australian Open and 6-4, 6-7 (5), 6-1 at Indian Wells. Perhaps the third time will be the charm for the 20-year-old Canadian, who reached the US Open final in 2021. Garcia's only 11-9 in her career at Wimbledon while winning at least 15 matches at each of the other four Grand Slams, and the No. 5 seed is just 9-8 in her last 17 matches. Coming off a women's doubles final run at the French Open to help her confidence, Fernandez may finally get over the hump against Garcia here after playing her tight twice.
Honorable Mentions
Alize Cornet (+475) vs. Elena Rybakina
Wimbledon Odds: Lock It In
Oscar Otte (-210) vs. Daniel Elahi Galan
Otte's been a tough out at Wimbledon in his two previous appearances. He pushed Andy Murray to a fifth set in the second round in 2021 and lost to Carlos Alcaraz in the third round last year. The German has a highly favorable second-round matchup here against Galan, who is just 3-12 in tour-level matches in 2022. Galan knocked off No. 24 seed Yoshihito Nishioka in the first round, but that result isn't all that impressive when you consider that Nishioka's career win-loss record on grass is 1-9.
Frances Tiafoe (-450) vs. Dominic Stephan Stricker
Tiafoe has a comfortable second-round matchup against the 20-year-old Stricker. Stricker has had some nice results on the Challenger circuit this year, but like most young players, he isn't very familiar with grass or best-of-five tennis. The 117th-ranked lefty did well to qualify into the main draw and then outlast Alexei Popyrin in a five-setter that concluded Wednesday, but Stricker's tank may not be full for Thursday's matchup with Tiafoe, who is ranked No. 10 in the world and possesses a booming serve, the effectiveness of which is amplified on grass. Dating back to Wimbledon last year, Tiafoe has won his last four second-round matches at Grand Slams while dropping just one set across the four matches combined.
Honorable Mention
Victoria Azarenka (-425) vs. Nadia Podoroska
Wimbledon Predictions: Value Bets
Stefanos Tsitsipas (+120) vs. Andy Murray
Murray's certainly capable of winning this match, but Tsitsipas shouldn't be viewed as the underdog here by any means at this stage in their respective careers. The No. 5 seed was pushed to 10-8 in the fifth-set match tiebreak by former US Open champion Dominic Thiem, so Tsitsipas will be battle-tested for this Center Court battle against the two-time Wimbledon champ. Much like Thiem since his wrist injury, Murray hasn't been the same player since having multiple surgical procedures on his hip in 2018 and 2019. The former world No. 1 has displayed his best form since that point in 2023, but he's still ranked just 40th in the world. Murray's chances against Tsitsipas head to head are highest on grass, and he won the only previous grass-court meeting between the two in 2022 to avenge Tsitsipas' thrilling five-set victory at the 2021 US Open, but at the end of the day, this will still be Tsitsipas' match to lose. If these two played out this match 10 times, Tsitsipas would likely win six or seven.
Anett Kontaveit (+155) vs. Marie Bouzkova
Kontaveit will be saying goodbye to professional tennis whenever her Wimbledon run concludes, but the former world No. 2 should be able to keep her career going for at least one more match. The Estonian won the only previous encounter between these two 6-3, 6-3 in 2020, and while she hasn't spent much time on the practice courts recently due to the degenerative back condition that's forcing her to retire, Kontaveit also finally has the chance to play freely in a Grand Slam knowing that the pressure's off her here. Bouzkova's seeded No. 32 and made the Wimbledon quarterfinals last year, but she's just 12-16 in 2023 and came into this tournament on a four-match losing streak.
Honorable Mention
Denis Shapovalov (-160) vs. Gregoire Barrere
