The 2026 edition of Wimbledon is officially underway at the All England Club in London. We’ve broken down the day’s best tennis betting picks, digging into matchup tactics, surface tendencies, and current form to find the sharpest edges on the board. Whether you’re betting the moneyline, game spread, set spread, or total, our 2026 Wimbledon best bets are designed to help you profit. I’m dropping some of my favorite plays for Tuesday, June 30 below, but make sure you also monitor the picks page. I usually have a few more picks over there, plus I occasionally add plays based on the way lines are moving. That’s also where Gill Alexander posts his bets.
Robin Montgomery vs. Jasmine Paolini
This is one of the fishiest lines you’ll see all tournament. Paolini, a Wimbledon runner-up in 2024, is a well-known player, she’s Top 20 in the rankings, and she has a massive fanbase. Meanwhile, Montgomery sits at No. 195 in the world.
Our VSiN betting splits show an overwhelming amount of support for Paolini here, yet Montgomery is a pretty heavy betting favorite. That suggests there’s sharp action on Montgomery to win.
It isn’t hard to see why the smartest bettors in the world are backing Montgomery. Paolini is just 12-12 since the start of the 2026 season, her last few losses have been very demoralizing, and Montgomery won a title in ‘s-Hertogenbosch a couple of weeks ago. The southpaw beat some solid players in the process too.
Montgomery just enters this match in much better form. That said, I’m loading up on the American, even though Paolini is a better overall player.
Bet: Montgomery ML (-166 – 1.5 units)
MORE: I have WAY more picks for this Wimbledon slate. VSiN Pro subscribers can check them out here!
Sofia Kenin vs. Petra Marcinko
Kenin looked like she was making strides last season, going 27-26 after a 2025 season in which she went 14-22. All of a sudden, Kenin is back to looking miserable. She’s 3-13 since the start of 2026, she has lost three consecutive matches, and her play has just been insanely erratic. So, why am I backing her to beat Marcinko? The pricing.
The last time we saw Marcinko, the Croatian retired after losing the first of her match against Madison Keys in the Eastbourne semifinals. Well, that match was only four days ago. Are we sure she’s 100% here?
Kenin also happens to be 14-12 on grass in her career. Even with this grass-court season going poorly, her game has always been a nice fit for grass. She can pound shots from the baseline, taking them early and making opponents rush. She can also mix in drop shots and utilize her backhand slice. If she just shows up and plays her C+ or B- game, she’ll have a chance here. We just need her to avoid the very clear F-level game she has displayed all year.
Bet: Kenin ML (+126)
Mackenzie McDonald vs. Patrick Kypson
Stan Wawrinka vs. Matteo Berrettini
To close out the slate, I’m going with a two-leg parlay that calls for McDonald and Berrettini to win.
McDonald got stronger and stronger throughout qualifying, winning his final two matches in straight sets. That isn’t lost on me, as McDonald has always been a dangerous grass-court player. While it might not seem like much, McDonald does have 19 wins on this surface. Meanwhile, Kypson has played only one main-draw match on grass in his career. We also haven’t seen Kypson since the Rome Masters. That said, I’ll take McDonald’s experience over Kypson, who should be a bit lost on this surface. He should also be rusty.
To get a better price on McDonald, I’m taking Berrettini to beat Wawrinka. The last time we saw Berrettini, the Italian had to withdraw in his match against Matteo Arnaldi in the French Open quarterfinals. But if he’s even remotely healthy, his big serves and forehands should be tough for an older Wawrinka to overcome. Berrettini is very tough to beat on grass, which is why he was a runner-up here in 2021.
PARLAY: McDonald ML & Berrettini ML (-130 – 1.5 units)
2026 W-L Record: 887-1025 (+6.92 units)
