Both Wimbledon men's semifinals will be played Friday on the grass courts of the All England Club in London. Three familiar faces are joined by a home underdog for Friday's action, which is highlighted by the most anticipated match of the tournament.
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All men's singles matches at Grand Slams are best of five sets. A mix of players' previous grass court results, recent form and stylistic matchups can help pinpoint intriguing betting opportunities in Friday's men's semifinal matches.
Wimbledon Tennis Picks: Sinner vs. Djokovic
Jannik Sinner (-459) vs. Novak Djokovic (+341)
Sinner had dominant streaks of five consecutive matches and nine consecutive sets won against Djokovic prior to their meeting at this year's Australian Open, when Djokovic shocked the favored Italian, 6-4 in the fifth. Their last meeting prior to that was a straight-set Sinner win at Wimbledon en route to the title in 2025, but Djokovic defeated Sinner at Wimbledon twice as the Serb built an early 4-1 edge in a head-to-head that now stands 6-5 in Sinner's favor. In this year's tournament, Sinner has had to work much less hard to reach the semifinals, dropping only two sets (both in the first round against Miomir Kecmanovic) while benefiting from a ridiculously easy draw that hasn't seen him face an opponent ranked higher than 48th. Meanwhile, Djokovic has dropped five sets through five matches.
Sinner's level of play here has been subpar by his lofty standards, which says a lot about just how good he is to still cruise into the semifinals but also leaves the door open for Djokovic to pull an upset like the one we saw in Melbourne. Assuming Djokovic is close to fully recovered from his five-hour and 14-minute, five-set quarterfinal marathon against Felix Auger-Aliassime (having two days off instead of the usual one should help significantly in that regard), it's fair to say that Sinner will need to play his best match of the tournament so far to advance. If Sinner continues to spray forehands, he won't be able to rely on his serve to consistently bail him out against the greatest returner of all time the way he could against lesser competition in the earlier rounds. Djokovic certainly has a puncher's chance in this match given what we have seen so far in this tournament, especially on grass where the 39-year-old can shorten points with either power or variety when needed.
Wimbledon Men's Semifinal Prediction: Djokovic def. Sinner 6-4, 3-6, 7-6, 1-6, 6-4
Wimbledon Tennis Picks: Zverev vs. Fery
Alexander Zverev (-700) vs. Arthur Fery (+478)
Zverev stretched his Grand Slam winning streak to 12 consecutive matches with his straight-set quarterfinal win over Taylor Fritz, which snapped a seven-match personal losing streak against the American. The French Open champion is playing with a newfound freedom after getting that weight lifted off his shoulders with his first Grand Slam title, and he has dropped only two sets en route to the first Wimbledon semifinal and 12th Grand Slam semifinal of his career. The No. 2 seed is 4-7 in his previous 11 major semifinals, but Fery is the weakest opponent Zverev has faced at this stage, at least on paper.
Fery's Cinderella run has included a mix of clutch play and dominance, ranging from consecutive fifth-set tiebreak wins over Zizou Bergs and Grigor Dimitrov to his straight-set sweep of Flavio Cobolli in the quarterfinals. Prior to upsetting the ninth-seeded Cobolli, the 114th-ranked Brit hadn't faced a seed in this tournament, and he certainly hasn't been tasked with returning a serve of Zverev's caliber. Fery's run fueled by the support of his home country's fans is reminiscent of Lois Boisson's 2025 French Open run on the women's side, which flamed out in the semifinals. We could see a similar result here as Fery tries to handle the moment in the biggest match of his life against Zverev, who is playing the best and most confident tennis of his career.
Wimbledon Men's Semifinal Prediction: Zverev def. Fery 6-2, 6-7, 7-6, 6-4
