Wimbledon Picks & Predictions for Wednesday, July 9 – Shelton vs Sinner, Djokovic vs Cobolli

• The men’s quarterfinals continue on Wednesday with Ben Shelton vs Jannik Sinner, and Novak Djokovic vs Flavio Cobolli
• Sinner and Djokovic are both massive favorites to win their respective matches, but both struggled somewhat in the round of 16
• Below, see my favorite Wimbledon picks and predictions for Wednesday, July 9

Just six players remain in the men’s portion of the Wimbledon bracket. American Taylor Fritz already punched his ticket to the semifinals on Tuesday, and compatriot Ben Shelton is hoping to do the same on Wednesday. But Shelton will have to take down world #1 Jannik Sinner if he’s going to reach his first-ever grand slam semi.

After Sinner/Shelton, living legend Novak Djokovic will take the court against up-and-coming Flavio Cobolli, who has already established a career-best grand slam performance by reaching the quarters.

In the table below, I have set out my favorite Shelton/Sinner Djokovic/Cobolli picks for Wednesday’s Wimbledon quarterfinals.

Wimbledon Picks & Predictions for Wednesday, July 9

I am targeting …

Odds as of 1:59 pm ET, July 8. Find the top sportsbook promos to use during Wimbledon 2025.

Sinner vs Shelton Picks & Prediction

It’s hard to know what to do with Jannik Sinner right now. Not only did he suffer a stunning upset loss to Alexander Bublik in the second round in Halle (3-6, 6-3, 6-4), he was two sets down to #21 Grigor Dimitrov (3-6, 5-7, 2-2) in the round of 16 on Monday before the Bulgarian was forced to retire with a pectoral injury.

That result was all the more surprising given how consummately he waltzed through his first three opponents (#95 Luca Nardi, #92 Aleksandar Vukic, and #52 Pedro Martinez), holding all 37 service games and finishing at least +11 in games in all three matches. Only one of his first three opponents even managed to win four games in a single set.

Sinner suffered his own injury (elbow) early against Dimitrov and he canceled his practice session on Tuesday. He was scheduled for an MRI on Tuesday afternoon.

World #10 Ben Shelton struggled badly in the Wimbledon build-up, going 0-3 on grass with a trio of straight-set defeats against #72 Arthur Rinderknech, #62 Lerner Tien, and #53 Tomas Martin Etcheverry, who’s really more of a clay-court specialist.

But that poor form was shrugged off immediately once Wimbledon started. Shelton posted straight-set wins over #179 Alex Bolt (6-4, 7-6¹, 7-6⁴), #87 Rinky Hijikata (6-2, 7-5, 6-4), and #105 Marton Fucsovics (6-3, 7-6⁴, 6-2) before coming from a set down to oust #47 Lorenzo Sonego (3-6, 6-1, 7-6¹, 7-5).

But the next set that Shelton wins against Sinner will be the first in the last five matches. The pair have met five times since October 25, 2023, with the Italian winning each one in straight sets. Shelton won their first-even meeting (2-6, 6-3, 7-6⁵). Five of their career matches were on hard courts; the other was at Wimbledon last year, when Sinner cruised to a 6-2, 6-4, 7-6⁹ victory.

I am going to chalk-up Sinner’s poor play against Dimitrov to the elbow injury. If he’s well enough to play on Wednesday, I expect him to once again dominate a familiar opponent. Given the potential for the injury to hamper him, I’m not interested in a straight moneyline wager on Sinner to win at short odds (-300 or shorter across sportsbooks).

Instead I’m targeting a much longer price on a first-set wager. The best price on Sinner to win the first set is currently -188 at FanDuel. That prop is as short as -250 at bet265. If Sinner retires during the first set, the wager will be voided.

Pick: Sinner to win 1st set (-188 at FanDuel)

Djokovic vs Cobolli Picks & Prediction

Djokovic and Cobolli have only met once before, back in October 2024 on hardcourts in Shanghai, and it was an absolute beatdown for the GOAT. Djokovic held all eight of his service games and broke on 57% of return games during a dominant 6-1, 6-2 victory. Cobolli served a respectable 64% on first serves, but only won 54% of first-serve points.

Djokovic served just 60% but won over 80% of both first-serve and second-serve points. Cobolli didn’t generate a single break point in the entire match.

Cobolli’s serve has been much improved throughout the 2025 grass-court season, with the exception of a 6-2, 6-2 upset loss against Jacob Fearnley in the first round in Eastbourne. He beat 18-year-old prodigy Joao Fonseca in the first round in Halle (5-7, 7-6³, 7-6⁸) and followed up with a quality win over Denis Shapovalov (7-6², 4-6, 7-6⁵) before losing a competitive match to world #3 Alexander Zverev (6-4, 7-6⁶) in the quarters. He held 85% of his service games in Halle.

He’s been even better in his first four matches at Wimbledon against world #247 Beibit Zhukayev (6-3, 7-6⁷, 6-1), #281 Jacob Pinnington Jones (6-1, 7-6⁶, 6-2), #17 Jakub Mensik (6-2, 6-4, 6-2), and big-serving veteran Marin Cilic (6-4, 6-4, 6-7⁴, 7-6³), winning a jaw-dropping 97% of his 63 service games and losing just a single set (via tiebreak to Cilic).

The question becomes whether the 23-year-old will be able to overcome the significant mental hurdle of playing, not only a player of Djokovic’s stature, but one that crushed him so badly less than a year ago in their only previous meeting.

My instinct is that he won/t. Djokovic did look vulnerable against Alex de Minaur, getting broken six times during a 1-6, 6-4, 6-4, 6-4 win. But de Minaur is a significantly better returner than Cobolli and, on the whole, that was an anomalous performance from Novak, who had only been broken once in his first three matches (42 service games).

I am expecting another unmitigated annihilation in favor of the best grand-slam performer in men’s tennis history.

Pick: Djokovic to win in straight sets (-125 at bet365)