Steven Psihogios

Talents like Jannik Sinner and Novak Djokovic are featured in my round of 16 Wimbledon predictions.

The pregame narrative: Sinner is crushing the competition, and veteran Grigor Dimitrov is up next. Novak Djokovic is cruising at Wimbledon, which doesn’t bode well for Alex De Minaur. Lastly, Flavio Cobolli is a nice pick to beat Marin Cilic.

Check out my top Wimbledon predictions for July 7.

Wimbledon predictions: July 7

Best Bet: Cobolli to win (-110)

Cobolli still doesn’t appear to be getting his due respect.

The Italian earned an upset win over Jakub Mensik in the third round at The Championships as he continues to stack stellar results together.

He has now won 12 of his last 15 matches, including a title at the Hamburg Open.

It’s hard to knock Cobolli’s losses, either, as two of those three have come to Alexander Zverev.

Cilic is a bit of a grass specialist, going 97-35 on the surface in his career and 9-1 in 2025. His record this year does include seven matches at the Challenger level, though, which is worth mentioning.

Cilic boasts a dominant serve that has been troubling opponents for years. Cobolli has demonstrated a strong all-around game in recent matches and has a serve that plays well on grass. He has 24 aces to eight double faults at Wimbledon.

The two have never faced off on grass, but Cobolli does hold a distinct 2-0 series lead over the Croatian.

Best Bet: Sinner vs. Dimitrov

Sinner -7.5 games (-115): This has nothing to do with Dimitrov, who is playing some excellent tennis ahead of this contest.

The Bulgarian has only lost one set at The Championships so far, but will be facing a top-50 competitor for the first time at this tournament.

And he’s not facing just any top-50 player; he’s battling Sinner, who is in fine form at Wimbledon.

Check out Sinner’s results to this point in the tournament:

• vs. Luca Nardi (6-4, 6-3, 6-0)

• vs. Aleksandar Vukic (6-1, 6-1, 6-3)

• vs. Pedro Martinez (6-1, 6-3, 6-1)

Sinner has won all three of his matches by 11 games or more.

These two competitors have never squared off on grass, but Sinner has dominated the head-to-head history. The Italian boasts a 4-1 record, winning each of the last four meetings.

Ultimately, Sinner’s elite return skills should be able to convert breaks and cash this wager. The former is third in percentage of serve games won (29.1%) while the latter is 29th (21.7%).

Best Bet: Djokovic vs. De Minaur

Djokovic -2.5 sets (+138): I will continue betting on Djokovic to cruise on grass until he runs into Carlos Alcaraz or Sinner.

The Serbian has advanced to the final at the last six Wimbledons he has participated in and boasts an otherworldly 98-11 record on the surface.

De Minaur has played very well at The Championships, dropping only one set so far. The level of competition he has squared off against, however, leaves plenty to be desired, as he hasn’t faced anybody inside the ATP’s top-70 players.

Djokovic, meanwhile, has already dismantled two top-50 competitors and has covered this spread in each of his last two victories.

Ultimately, bettors can trust Djokovic to come through in the clutch moments of this match. He ranks 10th in under-pressure rating across the last 52 weeks, while De Minaur places 28th.

Wimbledon predictions made at 3:42 p.m. on 07/06/2025.

Jannik Sinner headlines Saturday’s Wimbledon action from the All England Club.

The pregame narrative: Sinner aims to inch one step closer to his first finals appearance at Wimbledon in his third-round match versus Pedro Martinez. Elsewhere, Flavio Cobolli battles Jakub Mensik, and Grigor Dimitrov takes on Sebastian Ofner.

Check out my top Wimbledon predictions for July 5.

Wimbledon predictions: July 5

Best Bet: Cobolli to win (+143)

Cobolli is a decently sized underdog in this matchup, but there is value backing him to win over Jakub Mensik.

Firstly, Cobolli has been stacking some very impressive results together ahead of this tournament. He won eight of his last 11 matches before arriving at the All England Club, including a tournament win at Bad Homgburg.

Two of his three losses during this stretch were to world No. 3 Alexander Zverev, and that’s certainly nothing Cobolli should be ashamed of.

Mensik wasn’t nearly as impressive, dropping four of his seven matches over the same period.

Secondly, he enters this matchup with the same record as Mensik on grass courts this year (4-2), proving that there is very little separating these two.

Lastly, Cobolli holds a noticeable serve advantage, which is notable on grass courts that favour stronger servers. The Italian ranks 65th in serve rating on grass over the last 52 weeks, while Mensik is 83rd.

Key stat: Cobolli is tied with Novak Djokovic for 28th among all ATP competitors in percentage of second serves won (55.9%).

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Wimbledon best bet: Dimitrov vs. Ofner

Dimitrov -2.5 sets (+200): It’s a little surprising to see that this is the first meeting between two tennis veterans.

Dimitrov, 34, and Ofner, 29, are not new to the All England Club. The former, however, is the only one who has had repeated success at this tournament.

Dimitrov has advanced to the fourth round in each of his last two runs at Wimbledon. His best finish at the tournament was a semifinal appearance in 2014.

Ofner earned a third-round appearance at Wimbledon in 2017, but hadn’t won a match at the tournament until this year.

The Bulgarian tennis star also owns a strong record on grass over the last three years. He’s 13-4 on the surface compared to Ofner’s 12-8 mark over the same stretch.

Dimitrov is also an elite server on grass, while Ofner isn’t. He ranks ninth in serve rating, while Ofner is 89th.

Dimitrov has only lost one set across two matches at Wimbledon. I expect him to cruise against the lowest-ranked player he’s faced yet (Ofner is world No. 165).

Best Bet: Sinner vs. Martinez

Sinner -10.5 games (-118): This is a large line for anybody to cover, but Sinner is making it look easy.

The Italian superstar has won twice by this margin already at the tournament. Sinner beat Luca Nardi by 11 games in the first round and Aleksandar Vukic by 13 games in the second round.

Martinez has only lost one set at Wimbledon through two matches, but playing Sinner is very different than battling Mariano Navone or George Loffhagen.

The Spanish tennis star is not having a great campaign. He’s a poor 13-20 overall, and his career record on grass is equally unimpressive.

Martinez is 6-12 on grass in his career.

Wimbledon predictions made at 12:35 p.m. on 07/04/2025.