Two top players in the world play quarterfinal matches at Wimbledon on Wednesday.
The latest: Jannik Sinner will be playing through an elbow injury against a streaking Ben Shelton. Starting just after that, Novak Djokovic looks to fend off a game underdog in Flavio Cobolli.
Check out my top Wimbledon predictions for July 9, featuring a pick on Iga Swiatek vs. Liudmila Samsonova.
Wimbledon predictions: July 9
Best Bet: Cobolli +2.5 sets (-105)
Cobolli is a massive underdog (+750) to beat Djokovic, which means the Italian has good value to win a set.
- The 23-year-old is at the top of his game right now, ranking the highest he’s ever been in the ATP (No. 23).
- He’s rolled through the competition at the All England Club, winning 12 of 13 possible sets. That includes two straight wins as an underdog.
There’s no denying that Djokovic is one of the best to ever do it on grass, sporting a 99-11 career record on the playing surface. But he’s allowed two of four opponents to take a set off of him at this event.
Cobolli’s been the better player, too. He needed over an hour less of time on court to reach the quarterfinal. There’s some stock in that.
It’s hard for someone playing as well as Cobolli to suddenly lose three straight sets, regardless of the opponent.
Go to full Wimbledon betting markets
Best Bet: Sinner vs. Shelton
Shelton +1.5 sets (+150): There is some major concern in the Sinner camp. In his match with Grigor Dimitrov, he injured his elbow before going down two sets and was in some serious trouble.
Dimitrov ended up having to retire in the third set with what appeared to be a pectoral injury. It was an unfortunate bounce that kept Sinner’s tournament alive.
Since then, the Italian cancelled practice and has an MRI scheduled for Tuesday to check for serious damage. If he is able to go, I’m certain he’ll be less than 100%.
And that’s not a good spot to be in against Shelton right now. The American has won three of his four matches at Wimbledon in straight sets. He’s also up to No. 10 in the world, the highest ranking of his young career.
The 21-year-old has saved 87% of his break points and won 95% of his service games on grass in 2025.
At 100%, I’d back Sinner in a heartbeat. But a concerning injury at this stage of the competition has me very worried for the Italian.
I’m officially putting this match on upset watch.
Best Bet: Swiatek vs. Samsonova
Swiatek -3.5 games (-130): The former world No. 1 looks in form right now and it’s a scary sight for her competitors.
- She’s 7-1 on grass this season (29-7 in her career overall).
- Six of those wins came in straight sets.
Her opponent, Samsonova, has also been playing really well, winning every set at Wimbledon, but she’s struggled in this matchup.
Swiatek is 4-0 vs. Samsonova in her career, winning the last three matches in straight sets and covering this spread in each of those meetings.
Wimbledon predictions made at 1:16 p.m. on 07/08/2025.
Spencer is a true sports junkie. A graduate of the Sports Journalism program at Centennial College, he first joined NorthStar Gaming as an intern in 2023. He is now a contributing writer. He loves finding the edge to bet on in all sports but has a deep passion for the NBA and UFC. Previous stops include Sportsnet.