Daniil Medvedev vs Marin Cilic Prediction 6/29/2026 Today’s Tennis Picks

Daniil Medvedev faces former finalist Marin Cilic in the first round of the 2026 Wimbledon Championships on Monday, June 29. It will be a clash of former one-time Grand Slam champions. Medvedev and Cilic faced off during the grass swing in mid-June. Will it be a repeat outcome? Here’s our Daniil Medvedev vs Marin Cilic prediction. This preview will include a Daniil Medvedev vs Marin Cilic pick.

Daniil Medvedev vs Marin Cilic Preview

Daniil Medvedev is the eighth seed at this year’s Wimbledon. This is also his eighth participation in the main draw at the All England Club. He has twice made it to the semifinal stage, and was stopped by eventual champion Carlos Alcaraz. Last year, the Russian succumbed to a first-round exit at the hands of Benjamin Bonzi.

Medvedev has compiled 28 wins and 11 losses this season. On grass, he has competed in two warm-up tournaments before Wimbledon. He reached the semifinals of the Libema Open, where he surprisingly lost to Kamil Majchrzak. His second tournament was in Halle, where the former World No. 1 bowed out in the quarterfinal stage against Daniel Altmaier.

Marin Cilic is ranked 60th in the ATP rankings and is set to make his 16th appearance at Wimbledon. Cilic achieved a career-best run by reaching the final in 2017, where he lost to Swiss legend Roger Federer. Before that, the Croatian reached three successive quarterfinals at the All England Club.

Cilic has picked up three grass-court titles during his career, with the most prominent of those being his 2018 success at Queen’s Club. He saved a match point to beat Novak Djokovic in the final.

Cilic has compiled 13 wins and 13 losses in 2026. Like Medvedev, he has played in two warm-up events. He lost to Medvedev in the quarterfinals of the Libema Open, while this past week, he was knocked out in the first round at Queen’s by Ugo Humbert.

Daniil Medvedev vs Marin Cilic Head-To-Head

Medvedev and Cilic have met five times. Medvedev holds a healthy 4-1 lead in the head-to-head and owns 2 career victories on grass.

Daniil Medvedev vs Marin Cilic Prediction

Both previous meetings on grass were very competitive and at least one tiebreak feels very much in play in this one, with four or potentially five sets being the outcome. I still feel Medvedev will have full control of this match the longer it goes. With that being said, the over 38.5 games looks very appealing here.

Nur Said's Pick: Over 38.5 games in the match