Jannik Sinner vs. Ben Shelton Prediction, Odds for Wimbledon Quarterfinal (Can Bettors Trust Sinner?)

Can Ben Shelton pull off an upset in the quarterfinals at Wimbledon?

Ben Shelton is a major underdog in the quarterfinals against Jannik Sinner. / Susan Mullane-Imagn Images

Jannik Sinner is in the quarterfinals for the fourth straight year at Wimbledon, but he got a lucky break on Monday to get there.

The Italian was down two sets against Grigor Dimitrov in the fourth round, but an injury to Dimitrov forced him to retire, giving Sinner a spot in the quarters. However, the Italian did not escape unscathed, as he underwent an MRI after a hard fall on Monday. 

It’ll be interesting to see how he feels in a practice session on Tuesday and if the injury will impact him against his quarterfinal opponent, American Ben Shelton.

These two players are two of the best servers in the game, and Shelton (the No. 10 player in the world) dominated Italian Lorenzo Sonego in the final three sets of their match after dropping the first set.

Shelton is still set as a massive underdog against Sinner, but can the American take advantage with the world’s No. 1 player potentially banged up?

Let’s take a look at the odds, the path for each player to get here, and my prediction for this quarterfinal match. 

Jannik Sinner vs. Ben Shelton Odds

Odds via DraftKings Sportsbook.

Moneyline

• Jannik Sinner: -400
• Ben Shelton: +310

Total

• 39.5 (Over -115/Under -115)

Jannik Sinner vs. Ben Shelton How to Watch

• Date: Wednesday, July 9
• Time: 9:30 a.m. EST
• How to Watch (TV): ESPN/ESPN+

Jannik Sinner: How Did They Get Here?

Sinner has thrived at Wimbledon in recent years, making a semifinal appearance in 2023 and quarterfinal appearances in 2022, 2023, and 2024. However, he has not made a final at the All England Lawn Tennis and Croquet Club in his career.

Prior to struggling against Dimitrov in the fourth round, Sinner had dropped just 17 games over his first three matches. That’s a positive sign for his play in this tournament, but his injury is certainly concerning since Dimitrov had him on the ropes on Monday. 

Sinner knocked Shelton out of Wimbledon with a Round 4 win in 2024, and he beat him earlier this year in the semifinals of the Australian Open. Can he continue his dominance against the American? 

Ben Shelton: How Did They Get Here?

Shelton won each of his first three matches in straight sets before dropping the first set of his fourth-round matchup with Sonego. 

However, the American rebounded to win the next three sets 6-1, 7-6, and 7-5, sending him to the quarters for the first time in his career at the All England Lawn Tennis and Croquet Club.

Last year, Shelton lost 6-2, 6-4, 7-6 to Sinner in the Round of 16 at Wimbledon, and he has not won a set against the Italian since beating him in 2023 at the TP Masters 1000 Shanghai.

Overall, Sinner has a 5-1 record against Shelton in their head-to-head meetings. 

Jannik Sinner vs. Ben Shelton Prediction and What the Odds Say

Based on the odds, Sinner is expected to advance to the semifinals, as he has an implied probability of 80 percent since he’s a -400 favorite. 

However, I am not sold on the Italian walking over Shelton in this match, especially since he could be banged up. Sinner did not look effective against Dimitrov, and he would have needed a shocking comeback to advance to the quarterfinals had Dimitrov not gotten hurt. 

Meanwhile, Shelton has been fairly dominant in 2025 at Wimbledon, and he does have a semifinal appearance at a Grand Slam under his belt this year.

Sinner has dominated this matchup in recent years, winning each of the last five meetings against Shelton, but I have a bet that I think is worth taking for the American.

Bettors are going to have to lay some juice, but I don’t mind taking Shelton to win a set at -225 odds. The set spread for Shelton +2.5 (meaning he needs to win one set) is intriguing, and if you take it down to +1.5 (meaning he needs to win two sets), the price is +135.

If Sinner is at less than 100 percent, I think Shelton can carry his way to some wins with his impressive serving ability. 

Instead of betting on Shelton to pull off the upset, I think this wager gives bettors a little more wiggle room in this quarterfinal matchup. Either way, I’m worried about how Sinner will hold up after a shaky Round 4. 

Pick: Shelton +2.5 Sets (-225 at DraftKings)

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Odds refresh periodically and are subject to change.

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