This article is part of our Tennis Picks series.
Both men's semifinals at Wimbledon are scheduled to be played Friday. These were the four players with the best pre-tournament odds of winning the title, so chalk has prevailed up to this point, setting up some juicy semifinal matchups. Despite being among the favorites heading into this tournament, three of the four players are making their first Wimbledon semifinal appearances, while the fourth is a seven-time champion at the All England Club. 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. 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.
Wimbledon Odds: Djokovic vs. Sinner
Novak Djokovic (-550) vs. Jannik Sinner (+425)
Sinner had a two-set lead over Djokovic in the quarterfinals of Wimbledon last year before Djokovic came back to win in five sets. The 23-time Grand Slam champion went on to win the tournament for his fourth consecutive Wimbledon title and seventh overall. With an extra year of experience under his belt, Sinner will try to replicate last year's fast start but finish the job this time. Thanks to a favorable draw that hasn't included a single seeded opponent up to this point, Sinner has expended minimal energy en route to his first Grand Slam semifinal, dropping only two sets.
Djokovic has also lost only two sets, but he's had trickier matches, having won five tiebreak sets and faced two top-20 seeds. Nobody has beaten Djokovic at a Grand Slam since Rafael Nadal at last year's French Open, but Sinner came close last year, and his power off both wings should allow him to stay on the front foot in a way Andrey Rublev failed to do against Djokovic after the first set in the quarterfinals due to Rublev's exploitable backhand. It will take a near-perfect effort from Sinner to stop Djokovic's march toward the first calendar slam since Steffi Graf in 1988, but the 21-year-old Italian is one of the few people capable of keeping pace with the decorated champion.
Wimbledon Prediction: Sinner def. Djokovic 6-4, 6-7, 6-4, 3-6, 7-6
Wimbledon Odds: Alcaraz vs. Medvedev
Carlos Alcaraz (-250) vs. Daniil Medvedev (+205)
This is the first Wimbledon semifinal appearance for both of these players, but the 20-year-old Alcaraz is likely to be back at this stage many times, while the 27-year-old Medvedev may not replicate this success at the grass court Grand Slam again. Medvedev hasn't faced a seeded opponent and needed five sets to get past Christopher Eubanks in the quarterfinals. The world No. 3 isn't nearly as comfortable moving on grass as hard courts, and Medvedev lost to Alcaraz 6-3, 6-2 on the hard courts of Indian Wells in March.
In their only other meeting, Medvedev defeated Alcaraz easily at Wimbledon two years ago, but Alcaraz has grown substantially as a grass court player since then. The world No. 1 was superb in his straight sets quarterfinal victory over sixth-seeded Holger Rune, and Alcaraz's unparalleled combination of power, speed and finesse is likely to overwhelm Medvedev here.
Wimbledon Prediction: Alcaraz def. Medvedev 7-5, 6-2, 4-6, 6-4
