Jannik Sinner vs Grigor Dimitrov Prediction, Pick, Odds for Wimbledon Round of 16

Jannik Sinner and Grigor Dimitrov will meet in the Wimbledon Round of 16 on Monday, July 7. The match will tentatively start at 11:20 a.m. ET and will be broadcast on ESPN and ESPN+.

Sinner, the World No. 1 has shown no mercy in the first three rounds of Wimbledon, winning every set with ease. He will face a recovered Dimitrov in this exciting top servers' duel.

Find my Wimbledon betting preview and Sinner vs Dimitrov prediction for Monday below.

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Jannik Sinner vs Grigor Dimitrov Prediction

• Sinner vs Dimitrov Pick: Under 31.5 (-120, BetMGM)

My Sinner vs Dimitrov best bet is Under 31.5 total games. Make sure to find the best odds by checking our live Wimbledon odds page.

Sinner vs Dimitrov Odds

Carlos Avilan's Sinner vs Dimitrov Preview, Prediction

Jannik Sinner Betting Preview

Watching Jannik Sinner play and imagining he could actually lose — let alone a match, just a set — sometimes feels like a work of fiction.

He is the closest to a movie villain — or perhaps Terminator, if you're a fan and prefer him to end up the hero — with no apparent weaknesses, making him impossible to defeat.

However, it has happened three times this year, as his 19-3 record shows. The first two times, of course, it was Carlos Alcaraz who did it.

The Spaniard seems to be the one with the formula — both victories were on clay in Madrid and Paris. Sinner's other loss was against Alexander Bublik on Halle's grass right before this tournament.

Sinner ranks among the best five servers in the ATP Tour and also the top three returners. He is the leader of the Under Pressure ranking, which takes into account the performance on break-point chances and tiebreaks.

In London, no one has been able to take even a set from Sinner. The Italian has won all nine sets over the first three rounds, and four of those sets were 6-1, and another one was a donut: 6-0.

Since he lost to Daniil Medvedev in five sets at last year's Wimbledon quarterfinals, Sinner has more tournament titles than losses: six to five (with three of those losses in that span against Alcaraz).

So you might be picking up on the trend: unless your last name is Alcaraz, chances are you're going to lose to Sinner.

Grigor Dimitrov Betting Preview

Injuries have recently limited Grigor Dimitrov, who has one of the worst streaks in Grand Slam history with four consecutive retirements.

The Bulgarian player was once compared to Roger Federer due to his fluid motion on serve and his hitting technique. Now, he can only be grateful for being pain-free. His recent leg injury has not flared up, and he has enjoyed a great first week at Wimbledon.

Dimitrov's main weapon is his serve. He has racked up 37 aces in the previous three rounds, five more than Sinner. One issue, though, is recurrent double faults: he already has 77 in 2025 while achieving 144 aces.

Another concern is that the Italian excels at returning, so he could be able to cancel or limit such strength.

However, Dimitrov should focus on what he has done well in this tournament, which is a lot: only one set lost, a 62% first-serve success rate, 82% first-serve points won and three hard-fought victories.

Whatever happens next is a welcome bonus for him.

Sinner vs Dimitrov Predictions, Betting Analysis

Wimbledon's official site estimates Sinner's likelihood to win at 84% — that seems to be underestimating him.

The Italian has the upper hand against Dimitrov in their career head-to-head, with four wins in five matches, all of those in a row since the Bulgarian beat him in their first encounter back in 2020.

The World No. 1 reached the Wimbledon semifinals in 2023, his most notable achievement in London to date.

This time, he will stop at nothing until the final, with a possible rematch against Alcaraz on his mind.

Pick: Under 31.5 (-120, BetMGM)