Marin Cilic takes on eighth seed Daniil Medvedev in the second match on No.1 Court at Wimbledon on Monday.
Both are former Grand Slam champions who have enjoyed moments of brilliance on the lawns of SW19.
Between them, they have reached three Wimbledon semi‑finals and one final, yet both arrive with questions to answer.
Cilic, who lost the 2017 men’s singles final to Roger Federer, has not reached the last eight since that run and has won just seven matches at Wimbledon in the intervening years.
Injuries have dogged the latter part of the 37-year-old’s career but he re-entered the top 100 just before last year’s Wimbledon and knocked out No.4 seed Jack Draper in round two.
Now 37, he enters his 16th main‑draw appearance hoping to avoid a first‑round exit for the first time since 2011.
Medvedev, meanwhile, made back‑to‑back Wimbledon semi‑finals in 2023 and 2024 but suffered a shock first‑round defeat last year to Benjamin Bonzi. His relationship with grass is complicated — sometimes sublime, sometimes erratic — and his recent Slam record reflects that inconsistency.
The pair have already met on grass this month, with Medvedev winning a fluctuating contest 6‑2 3‑6 6‑1 in ’s‑Hertogenbosch before going on to reach the semi‑finals. That victory extended his head‑to‑head lead to 4‑1.
Marin Cilic v Daniil Medvedev Tips Summary
Best Bet – Medvedev -4.5 Games @ 1/1
Alternative Bet – Medvedev to win & Both Players to Win a Set @ 6/5
Bet Builder – Over 39.5 Games, Medvedev will Not Break Serve in Set 1 & Medvedev will Win from Behind @ 15/2
Marin Cilic v Daniil Medvedev Prediction
Best Bet: Medvedev -4.5 Games @ 1/1
Medvedev’s recent grass‑court form — semi‑finals in ’s‑Hertogenbosch and quarter‑finals in Halle — suggests he is trending upward at exactly the right time.
His flat, skidding groundstrokes are tailor‑made for grass, and his return game remains one of the most disruptive in the sport.
Cilic remains capable of beating Medvedev on grass, although he is far removed from his peak. While he still delivers patches of elite serving, his movement and defensive coverage have declined.
His straight-sets defeat to world no.30 Ugo Humbert at Eastbourne exposed his frailties on return against another elite server.
Given Medvedev’s superior rally tolerance and recent head‑to‑head success, he should create enough separation to clear this handicap.
Alternative Bet: Medvedev to win & Both Players to Win a Set @ 6/5
Despite Medvedev’s edge, Cilic remains a threat on grass because of his serve — still a top‑tier weapon.
The Croat has taken sets off Medvedev in both of their grass‑court meetings — including at Wimbledon in 2021, where he led by two sets before the Russian mounted a comeback.
Medvedev’s early‑round matches often start slowly, and he has come undone against big servers who deny him rhythm.
The 30-year-old has lost the opening set in eight of his last nine matches in Grand Slams.
It is also noteworthy that six of the Russian’s last 10 such matches have gone to a fifth set.
Cilic can take a set if he strings together a few high‑percentage service games.
But over best‑of‑five, Medvedev’s consistency and physicality should prevail.
Marin Cilic v Daniil Medvedev Bet Builder
- Over 39.5 Games
- Medvedev will Not Break Serve in Set 1
- Medvedev will Win from Behind
Pays 15/2
This Bet Builder leans into the patterns of their two previous grass‑court meetings — both of which went the distance.
There were 48 games in their 2021 Wimbleon clash and 27 in their most recent tussle.
With two elite servers and a fast surface, long sets and tie‑breaks are highly likely. Even a four‑set match can comfortably exceed this line.
Cilic’s first‑serve percentage is typically highest in opening sets, and Medvedev’s deep return position can be less effective before he adjusts to pace and trajectory, so back the Croat not to be broken in the opener.
Medvedev has dropped the first set in four of his last six Slam openers. He also trailed Cilic by two sets at Wimbledon in 2021 before roaring back. A comeback win for the Russian fits both players’ historical patterns.
Learn more about how Bet Builders work in our Bet Builder guide.
Key Match Stats
- Medvedev leads the head‑to‑head 4–1, including two wins on grass
- Both grass‑court meetings — Wimbledon 2021 and Den Bosch 2026 — went the distance
- Cilic won 88% of first serve points in the opening two sets against Draper at Wimbledon 2025
- Medvedev made back‑to‑back semi‑finals in 2023 and 2024 but lost in the first round last year
- Cilic has not been broken in the first set of three of his last four matches against Medvedev
- Medvedev has lost the first set in eight of his last nine Grand Slam matches
Read more tennis betting tips and predictions on site.
This article was written by a partner sports writer via Spotlight Sports Group. All odds displayed on this page were correct at the time of writing and are subject to withdrawal or change at any time.
