MatchDay Picks: Wimbledon Day 2

Four Wimbledon Day 2 Matchday Picks, where proven grass-court ability and favorable pricing create opportunities against inflated favorites.

Day 2 at Wimbledon presents one of the best betting opportunities of the tournament. The market has overreacted to recent winning streaks, big-serving reputations, and young talent while discounting proven grass-court experience and matchup advantages.

Rather than laying heavy prices with questionable favorites, I’m taking four underdogs whose odds simply don’t match the underlying numbers.

Please visit our Matchday Picks transparency page, and here are your Matchday Picks for Tuesday, June 30.

Tuesday’s Card

• Jasmine Paolini (+131) vs. Robin Montgomery
• Beatriz Haddad Maia (+202) vs. Maria Timofeeva
• Serena Williams (+124) vs. Maya Joint
• Yannick Hanfmann (+110) vs. Giovanni Mpetshi Perricard

Jasmine Paolini (+131) vs. Robin Montgomery

Robin Montgomery has become one of the hottest names entering Wimbledon after an impressive run through lower-level grass-court events, but this is a completely different test.

When Montgomery faces elite competition, the numbers tell a different story. Her dominance ratio falls to just 0.69 against Top 20 opponents, while her return game struggles to create consistent pressure. Even her biggest weapon—the left-handed serve—loses much of its effectiveness, with her ace rate dropping dramatically against better returners.

Paolini has already proven she can compete on the biggest stages in tennis. She understands how to win Grand Slam matches, and grass rewards experience as much as talent.

At plus money, I’m happy to back the proven player over the hot streak.

The Play: Jasmine Paolini (+131)

Beatriz Haddad Maia (+202) vs. Maria Timofeeva

This line is almost entirely based on recent form.

Haddad Maia enters Wimbledon on a six-match losing streak, and the market has punished her accordingly. That’s created an opportunity.

Timofeeva has compiled an excellent record over the past year, but much of that success has come on clay. Once the surface changes to grass, her efficiency drops significantly. Her dominance ratio falls well below elite levels, and her return game becomes far less effective.

Meanwhile, Haddad Maia has already proven she can excel on grass. Sometimes the best betting opportunities come when an accomplished player is priced solely on recent results instead of long-term ability.

I’m willing to buy low.

The Play: Beatriz Haddad Maia (+202)

Serena Williams (+124) vs. Maya Joint

This is the most fascinating line on the board.

The betting market appears to be focused almost entirely on Serena Williams’ lengthy singles layoff while ignoring what’s happening on the other side of the net.

Joint arrives at Wimbledon having lost 13 of her last 14 matches and has looked physically compromised during much of that stretch because of a recurring back issue. That’s not the profile I want to back as a favorite.

No one knows exactly what Serena has left, but Wimbledon has always rewarded elite serving and championship experience. Few players in tennis history have possessed more of either.

If Serena is physically ready to compete, this number offers real value.

The Play: Serena Williams (+124)

Yannick Hanfmann (+110) vs. Giovanni Mpetshi Perricard

Mpetshi Perricard owns one of the biggest serves on the ATP Tour, and that’s exactly why he’s become the favorite.

The problem is that tennis isn’t won with one shot.

His serve earns plenty of free points, but his return game remains one of the weakest among top-level players. That makes it difficult for him to separate from quality opponents and often forces matches into tiebreaks where just a handful of points decide everything.

Hanfmann is well equipped for this matchup. His return game is built to neutralize big servers, and his overall grass-court numbers have quietly been excellent over the past year.

When I can get plus money in what projects as a coin-flip match, I’ll take it every time.

The Play: Yannick Hanfmann (+110)

Final Thoughts

The goal isn’t simply to pick underdogs.

It’s to identify prices that have drifted too far because of public perception while backing players whose grass-court profiles offer better value than the market suggests.

Sometimes the best bet isn’t the better player; it’s the better number.

Phil Naessens

Phil Naessens has spent decades in sports as a broadcaster, author, journalist, professional tennis coach, and betting analyst. As the founder and editor of Crush & Rush News and host of the Crush & Rush Tennis Podcast, he combines firsthand coaching experience with years of sports media and publishing to deliver thoughtful tennis analysis, tournament coverage, player features, and transparent betting insights built around value, and not hype.