Wimbledon Predictions for Monday, June 29: Medvedev, Ruud

Generally considered the most revered of the four Grand Slams, Wimbledon gets underway on Monday, June 29.

On the men’s side, Carlos Alcaraz remains out due to injury, leaving defending Wimbledon champion Jannik Sinner as the heavy favorite to lift the trophy again, featuring a 1.58x payout to win Wimbledon on PrizePicks Team Picks. However, as we saw in the French Open just a few weeks back, even the otherworldly Sinner isn’t invincible against his non-Alcaraz competitors. 

For the women, Aryna Sabalenka is technically the favorite with a 3.7x payout to win Wimbledon, but this is the one major where she’s yet to reach the final. This should be a pretty wide-open ladies' draw.

But we have a long way to go before the final ball is struck, and the first round is already giving us some spicy matches to look forward to. 

Below, we’ll break down our Wimbledon predictions for Monday’s tennis slate, including winner payouts, key stats, and three tennis match predictions for PrizePicks.

Make your Wimbledon predictions on PrizePicks for Monday’s matches now!

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Wimbledon Predictions, Tennis Picks for Monday, June 29

Before we get into our Wimbledon predictions for Monday, here’s a quick look at the three matches we’re focusing on and the consensus favorites on PrizePicks Team Picks.

Marin Cilic vs. Daniil Medvedev — First Round

• Cilic – 3.22x payout | Medvedev – 1.31x payout

Casper Ruud vs. Hubert Hurkacz — First Round

• Ruud – 2.5x payout | Hurkacz – 1.49x payout

Alexandre Muller vs. Tommy Paul — First Round

• Muller – 14.28x payout | Paul – 1.02x payout

On PrizePicks Team Picks, a 2x payout means the result will return $200 on a $100 entry. A lower payout multiplier signals a higher implied probability of that result based on user picks.

Payouts are live at the time of writing and are subject to change. Tennis winner markets are available in 35 states.

Marin Cilic vs. Daniil Medvedev Prediction for Wimbledon — Monday, June 29

Match Winner Payouts: Cilic 3.22x | Daniil Medvedev 1.31x
Tournament Round: First Round
2026 Record Entering Wimbledon: Cilic 13-12 | Medvedev 28-11
Head-to-Head Record: Medvedev Leads 4-1
How to Watch: ESPN and the ESPN App

At 37 years old, Marin Cilic is nearing the finish line of a strong career that includes winning the 2014 US Open and reaching a world No. 3 ranking in 2018. Now ranked No. 60, he comes into this tournament one win above .500 and is no longer a serious threat to make deep runs in majors. That being said, he did reach the fourth round at Wimbledon last year, so the tank isn’t empty just yet.

Daniil Medvedev remains as unpredictable as ever, capable of reaching Grand Slam finals or flaming out as early as the first round. It’s been much more of the latter lately, as Medvedev has exited in the first round in four of the last five majors, which included a first-round exit at last year’s Wimbledon. And yet, he was also a back-to-back Wimbledon semifinalist in 2023 and 2024 and owns a 67.1% career win rate on grass, so he should be a contender here.

Medvedev comes in with a solid 4-2 record across his two grass tune-up events this month, and it just so happens he faced Cilic over that stretch, defeating the Croatian in three sets. Overall, Medvedev has lost to Cilic just once in five meetings, and that lone loss came on clay, which is easily Daniil’s least favorite surface.

Despite the Jekyll and Hyde nature of Medvedev’s performances, these two players are at different stages of their careers, and the 30-year-old Russian’s lopsided history against his opponent should give him confidence. 

Per Tennis Abstract’s Elo ratings, Medvedev has a 67.2% win probability over Cilic.

Make your Cilic vs. Medvedev prediction on PrizePicks now!

Marin Cilic vs. Daniil Medvedev Pick for Wimbledon on Monday

Cilic vs. Medvedev — 39 Total Games

While Medvedev has dominated the head-to-head against Cilic, their four matches on grass and hard courts have all been fairly tight battles. All four have included a tiebreak, and/or Cilic has won at least one set.

These two played each other at Wimbledon in 2021, and their match went five sets, leading to 48 total match games.

At 2025 Wimbledon, three of Cilic’s four matches went four sets. While Medvedev lost his opening match last season, it also went four sets and included two tiebreaks. 

Cilic remains a capable server, which could help him earn some easy holds against Medvedev despite being the underdog. The Croatian has logged a 12.2% ace rate on grass over the past 52 weeks, and the tour average among the top 100 players is around 10%. 

Casper Ruud vs. Hubert Hurkacz for Wimbledon — Monday, June 29

Match Winner Payouts: Ruud 2.5x | Hurkacz 1.49x
Tournament Round: First Round
2026 Record Entering Wimbledon: Ruud 23-12 | Hurkacz 10-13
Head-to-Head Record: Ruud Leads 3-1
How to Watch: ESPN and the ESPN App

Casper Ruud is a three-time major finalist who’s seeded 11th, yet he’s the underdog against a sub-.500 Hubert Hurkacz who’s barely ranked inside the top 100.

The reason? Ruud has never advanced past the second round at Wimbledon.

Due to clay being Ruud’s best surface, the grass season has never been his priority, and he’s typically elected to rest in between the French Open and Wimbledon rather than enter other grass events. He hasn’t played in a non-Wimbledon grass event since playing a match at Queen’s Club in 2022.

As a result, the Norwegian has amassed a mere 5-7 career grass record despite logging 476 matches on the other two surfaces.

Meanwhile, Hurkacz may have an underwhelming 2026 record and ranking, but he’s a former top-10 player and was a semifinalist at 2021 Wimbledon. His 62.8% grass win percentage is his best across the three surfaces, too.

However, Hurkacz has struggled to string together consecutive wins in tour-level events this season, and going 1-2 on grass ahead of Wimbledon didn’t alleviate concerns about his form.

Despite Ruud’s meh grass history, Hurkacz’s lackluster campaign could open the door for the Norwegian to advance. Ruud has never faced Hurkacz on grass, but his 3-1 head-to-head record might give him a mental boost. 

Tennis Abstract’s Elo ratings project a tight matchup but give a 52.6% win chance in favor of Ruud.

Make your Ruud vs. Hurkacz prediction on PrizePicks now!

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Casper Ruud vs. Hubert Hurkacz Pick for Wimbledon on Monday

Casper Ruud vs. Hubert Hurkacz — 40 Total Games

Despite Ruud’s poor track record at Wimbledon, he’s typically found himself in tight matches regardless of the final result. Dating back to 2021, Rudd has played in seven Wimbledon matches, and only two have finished in straight sets. The other five matches have gone 44, 44, 38, 39, and 50 total match games.

Hurkacz boasts a massive serve, flashing an absurd 17.3% ace rate in 2026. This lines up with him putting up a 17.4% ace rate across his three grass matches thus far, as well. Even with Hurkacz playing below his usual standards this year, he’ll be difficult to break, giving him a reasonable chance of extending this match to four or maybe even five sets.

Due to his dominant serve combined with a dip in his return game this season, Hurkacz has also frequently found himself in tiebreaks. In 2026, he’s tallied the fifth-most tiebreaks (22) among players in the top 100 despite playing only 23 tour-level matches. 

Alexandre Muller vs. Tommy Paul Prediction for Wimbledon — Monday, June 29

Match Winner Payouts: Muller 14.28x | Paul 1.02x
Tournament Round: First Round
2026 Record Entering Wimbledon: Muller 4-10 | Paul 30-12
Head-to-Head Record: Paul Leads 1-0
How to Watch: ESPN and the ESPN App

In terms of recent form, Tommy Paul and Alexandre Muller couldn’t be any farther apart entering Wimbledon.

Paul is fresh off finishing runner-up on the grass at Queen’s Club, and he also enjoyed a positive clay season, going 12-4 and winning a title in Houston. He’s one of three players to reach 30 wins in 2026, trailing only Alexander Zverev and Jannik Sinner.

In contrast to this, Muller has lost seven straight matches across all levels, and he hasn’t won a tour-level match since the beginning of April at Marrakech. Once ranked as high as 38th last summer, he’s now dropped to 125th.

Overall, Paul is rock-solid across all surfaces, and his 65.9% win percentage on grass is actually his best among the three. He failed to get past the second round at last year’s Wimbledon due to an injury, but he was a quarterfinalist in 2024.

Muller’s career history doesn’t provide much optimism, either, as the 29-year-old is 2-5 on grass, and he’s never reached even the third round at any major.

Tennis Abstract’s Elo ratings are high on Paul in this one, pegging him for an 89.1% win probability.

Make your Muller vs. Paul prediction on PrizePicks now!

Alexandre Muller vs. Tommy Paul Pick for Wimbledon on Monday

Alexandre Muller vs. Tommy Paul — 29 Total Games

During his seven-match losing streak, Muller has won only one set. None of those matches have come against opponents ranked inside the top 50. 

Over his career, Muller is 20-40 versus top-50 players and 4-23 versus top-20 players. Paul comes into Wimbledon as the world No. 24, and he’s been ranked as high as No. 8.

In Paul’s recent run to the Queen’s Club final, he won in straight sets in all four of his victories.

The American defeated Muller in their only meeting, 6-3, 6-1, in 2023.

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Make Your Wimbledon Predictions on PrizePicks

Following a wild French Open, what surprises will we see at this year’s Wimbledon? We can look forward to plenty of fun matches and storylines over the next two weeks, beginning with Monday’s first-round action.

Don’t wait until lock — make your Wimbledon predictions on PrizePicks now.

Pick players, predict More or Less on their stats like games won or aces, or make match winner predictions with Team Picks, available in 35 states!

Stay locked in on Playbook for daily Wimbledon predictions, tennis picks, and PrizePicks analysis throughout the tournament.