Wimbledon Predictions, Picks, Odds for Cilic vs Medvedev, Nakashima vs Pinnington Jones — 6/29

After a wacky French Open that featured multiple upsets and Alexander Zverev finally winning his first major, Grand Slam No. 3 of the tennis season — Wimbledon — starts on Monday.

Defending champion Jannik Sinner is in action — as is Novak Djokovic — but our experts are targeting two other matches for their Wimbledon best bets.

Continue reading below to find our two men's Wimbledon predictions and picks for Monday, June 29.

Wimbledon Predictions, Picks, Odds — Monday, June 29

Cilic vs Medvedev Odds

By Ryan Minion

As a former runner-up at Wimbledon to Roger Federer in 2017, Marin Cilic boasts a very impressive skillset on grass with extremely aggressive net play.

The 37-year-old Croatian relies heavily on his first-strike approach, using his massive serve and heavy forehand to dictate point and shorten rallies.

The incredibly slick perennial ryegrass surface that comes with playing at Wimbledon results in balls traveling at a far quicker pace than any other Grand Slam surface.

While the Wimbledon veteran has a style tailor-made for grass courts, 30-year-old former Grand Slam winner Daniil Medvedev has a very similar skillset that could pose some problems for the Croatian.

Medvedev boasts elite baseline skills, a strong return game and all-court coverage that's given some of the best players in the world fits in recent years.

The Russian utilizes a heavy-defensive counter-punching game from far behind the baseline, forcing his opponents to exert a ton of energy on return.

I fully expect Medvedev to be quite comfortable extending rallies and forcing Cillic into making some unforced errors. The two have met five times previously with the former Grand Slam winner earning four wins.

Though Medvedev typically favors hard courts, he made consecutive Wimbledon semifinals in 2023 and 2024, showing he's made massive strides on the grass surface.

Cillic should hang around early given his vast experience playing in the surface conditions in London, but Medvedev is the far more skilled athlete and should ultimately prevail in what I expect to be a close four sets. (A tiebreaker is likely given how these two serve.)

I expect the match to go over 38.5 games and for the Russian to win in four sets at a stellar +250 price.

Pick: Over 38.5 | Medvedev ‘Set Score 3-1’ (+250) 

Nakashima vs Pinnington Jones Odds

By Tudor Cosma

Brandon Nakashima is a huge favorite, so he should prevail. However, I don't think he'll do it in three sets.

He has a good, stable serve, through which helps him in the ace department. Recently he recorded three aces in a very short match with Ignacio Buse and then three against Francisco Cerundolo.

This isn't impressive, but at least he's faced players who are strong on return.

Jack Pinnington Jones is playing on his home court. He'll have the stadium on his side and is this also a surface that he likes. He is capable of winning a set.

Pinnington Jones is quite slow on the return. He allowed eight aces from Shapovalov and then six against Jack Draper.

I think Nakashima will record at least 10 aces and the better value could be on 15+ (+162).

Pick: Brandon Nakashima 10+ Aces (-225, bet365)