Wimbledon Quarterfinals Predictions & Best Bets 2025: Our Expert Picks at All England Club

We're featuring three expert picks for Wednesday's Wimbledon quarterfinals, including a best bet to advance, a situational long shot, and a solid minus-money prop.

Gary Pearson

Last Updated: July 8, 2025 5:00 AM EDT • 5 minute read

Pictured: Novak Djokovic after winning his Round of 16 match as we offer our Wimbledon Quarterfinals Predictions & Best Bets. Photo by Geoff Burke via Imagn Images

This edition of Wimbledon has served up more surprises on the women's side than Kinder can manage in a year's worth of production. On the men's side, at least at the top of the Wimbledon odds leaderboard, it is as chalky as the hands of Olympic weightlifters.

Our Wimbledon quarterfinals predictions and best bets sourced a modified best bet to advance, a situational long shot, and a five-star minus-money prop via our best sports betting sites featuring the seven-time champion.

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✅ Best bet to advance: Iga Swiatek 2-0 (+100 via DraftKings) ⭐⭐⭐⭐
✅ Best upset pick: Ben Shelton (+385 via FanDuel) ⭐⭐
✅ Best prop bet: Novak Djokovic 3-0 (-120 via DraftKings) ⭐⭐⭐⭐

Read on for the latest odds and full analysis of our best bets ⤵️

💪 Best bet to advance in quarterfinals

✅ Prediction: Iga Swiatek straight sets ⭐⭐⭐⭐
📊 Best odds: +100 via DraftKings ($10 to win $10)

Wimbledon Quarterfinals Predictions & Best Bets 2025 — Pictured: The Polish no. 1 in action at the All England Club as we offer our Wimbledon Quarterfinals Predictions & Best Bets. Photo by Susan Mullane via Imagn Images

Both players have enjoyed a relatively easy time of it thus far, with Iga Swiatek dropping one set and Liudmila Samsonova entering the quarterfinals without conceding a set.

Samsonova's flawless record is about to get sullied in a big way.

The only seeded player she's come across is no. 16 Daria Kasatkina, who is by no means a world beater.

The Russian endures recurring nightmares every time she plays the persistent Pole, with Swiatek winning all four. The last three meetings have been particularly disconcerting for Samsonova, who won more than two games in a set once.

DraftKings is the undeniable place to lock it in, as its even-money odds are superior to the rest of our best sports betting apps, all of which provide minus-money odds.

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🚨 Best upset pick in quarterfinals

✅ Upset pick: Ben Shelton ⭐⭐
📊 Best odds: +385 via FanDuel ($10 to win 38.50)

Ok, so hear me out before you scoff louder than Ben Shelton grunts after winning a pivotal point.

Jannik Sinner did not look right after injuring his elbow early in the Round of 16 match against Grigor Dimitrov, which he would have lost had it not been for the Bulgarian sustaining a serious injury.

Ordinarily, I wouldn't go near this bet as Sinner has won five straight matches against Shelton, all of which in straight sets. That makes it 12 successive sets for the imposing Italian.

So, this bet is predicated on Sinner's elbow not being 100% healthy, the status of which is challenging to ascertain. I'm willing to take a flier on it after seeing Dimitrov humble him.

If his elbow is fine, I still expect Shelton to finally win a set. DraftKings and FanDuel offer +385 odds, the joint-best value.

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💰 Best prop bet in quarterfinals

✅ Prop bet: Novak Djokovic straight sets ⭐⭐⭐⭐
📊 Best odds: -120 via DraftKings ($10 to win $8.33)

Expect vintage Novak Djokovic in his quarterfinals matchup against 22nd-seed Flavio Cobolli. The 24-time major winner endured his worst set ever at Wimbledon in the opener against Alex de Minaur, and he'll be hellbent on correcting that wayward 30 minutes.

Unfortunately for Cobolli, he's directly in the crosshairs.

They've only met once previously, with Djokovic winning 6-1, 6-2 last year at the Shanghai Masters. While it's been an admirable run for the 23-year-old Italian, whose previous best result at a major was the third round, it's about to come to a straight-sets end.

DraftKings again has the best price, offering -120. Caesars is at the other side of the spectrum, offering an unsavory -145.

💡 More Wimbledon predictions

Taylor Fritz vs. Karen Khachanov prediction
Cam Norrie vs. Carlos Alcaraz prediction
Wimbledon quarterfinals predictions

💵 Best tennis betting sites

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DraftKings Promo Code | Read our DraftKings Review
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Each betting site featured on SBR has been meticulously researched and selected by our team of experts. If you sign up through our links, we may get a commission.

Written by:
Gary Pearson

Gary Pearson has written professionally since 2010, focusing on sports betting since 2014. Before entering the sports betting space, he contributed to the Canadian Press, FanSided, the Hockey Writers, the Calgary Herald, and other publications. His work has also been featured in Sports Illustrated and Bleacher Report. Gary, who consumes sports like a blue whale devours plankton, has a penchant for writing predictions and analyses across several sports, including hockey, soccer, football, tennis, and more. He bets regularly, preferring single-game picks, props, and live betting. While there isn't a sport he has yet to dabble in, Gary prefers betting on soccer, hockey, and football. He studied at various post-secondary institutions, including the University of Calgary, SAIT Polytechnic, and Griffith University, located in Brisbane, Australia. Gary has a marketing degree and completed his bachelor's degree in journalism at Griffith University. He feels strongly that life experience is as essential as post-secondary education, helping formulate more accurate predictions and analyses. Gary believes that competing at a high level of amateur sports during his formative years helped him better understand an athlete's psyche and the nuances and complexities of a team's dynamic, both on and off the playing surface. He feels that knowledge is immeasurably important when offering his analytical expertise. He has lived on five continents and currently resides in Canada.