Wimbledon Picks, Predictions & Best Bets for Day 1 (Monday, June 30)

• Wimbledon 2025 starts on Monday, June 30, with a packed slate of both men’s and women’s singles matches
• Brimming with confidence, American Jenson Brooksby faces #31 Tallon Griekspoor
• See my Wimbledon picks, predictions, and best bets for Day 1 of the tournament on Monday, June 30

Wimbledon 2025 opens with a bang on Monday, June 30, thanks to a number of high-profile singles matches on both the men’s and women’s sides of the proceedings.

Wimbledon Picks & Predictions for Day 1 (June 30)

The odds in the table above are as of 3:00 pm ET on Sunday, June 29th. They are subject to change in the next 24 hours.

Wimbledon Pick #1: Brooksby vs Griekspoor Over 41.5 Games

Jenson Brooksby doesn’t have a penchant for long matches. Only one of his last ten matches has seen both players win a set. But he’s coming in confident on grass after reaching the final in Eastbourne.

Moreover, neither he nor opponent Tallon Griekspoor have a penchant for winning/losing grand-slam matches in straight sets. At the 2025 French Open, Griekspoor went four or more sets in each of the first three rounds (before retiring in the second set against Alexander Zverev). Brooksby won a four-setter against Jaime Faria before losing in straights to countryman Sebastian Korda. At the 2025 Aussie Open, Brooksby went over 3.5 sets in two of three matches.

Griekspoor also heads into Wimbledon is excellent form on grass. He won in Mallorca against a mediocre field, beating Ethan Quinn (world #95), Gabriel Diallo (#41), Flexi Auger-Aliassime (#27), and Corentin Moutet (#83) in the final.

Both of these guys are playing to well to lose in straights and I love the value on over 41.5 at plus-money.

Pick: Over 41.5 games (+100)

Click the following link to get a 30-day free trial of Fubo TV!

Wimbledon Day 1 Pick #2: Moutet -1.5 Sets vs Comesana

The first career meeting between Corentin Moutet and Francesco Comesana is more of a mismatch than the odds suggest, especially on grass. Moutet is playing some of the best grass-court tennis of his career – reaching the final in Mallorca last time out – while Comesana, a clay-court specialist – has lost four straight matches overall, including his only grass-court test of the season: 7-6⁶, 6-4 to Jenson Brooksby in Eastbourne.

Comensana has only played five career matches on grass (2-3 overall). Moutet has a solid 23-14 lifetime record on the carpet, which includes a stunning three-set victory over world #5 Taylor Fritz in London just two weeks ago. He might drop a set, but I also see him advancing comfortably against a relatively inexperienced opponent.

Pick: Moutet -1.5 Sets (-108)

Wimbledon Pick #3: Watson Moneyline vs Tauson

The last of my picks for day-one action is Briton Heather Watson to win outright as a big underdog (+340). World #23 Clara Tauson is certainly the more talented and fitter of the two players. She’s never been great on the grass, though, and the crowd will obviously be behind Watson.

The 33-year-old showed some spunk in her grass-court tune-ups, going 5-5 overall including a win over world #34 Yulia Putintseva. Tauson is 3-2 on grass this season but just 6-10 career. She’s priced like an inevitability against Watson. She’s anything but on her least-favorite surface against a crowd favorite.

Pick: Watson moneyline (+340)