Preview: Wimbledon: Marin Cilic vs. Daniil Medvedev - prediction, form, head-to-head

Two former Grand Slam champions face off on Monday, as Marin Cilic and Daniil Medvedev meet in the first round at Wimbledon.

While Cilic is a former finalist at SW19, he has not reached the last eight since 2017, and takes on a player seeking to avoid consecutive first-round exits at the Championships after last year's shock loss to Benjamin Bonzi.

Match preview

Cilic is far from his prime, but the former world No 3 still delivers on any surface when everything aligns.

The 37-year-old heads into his 16th main draw appearance at Wimbledon, aiming to avoid a first-round exit since 2011.

At his peak, the Croat reached three quarter-finals between 2014 and 2016 and one final in 2017, when he was defeated by an inspired Roger Federer.

However, that run marked the last time he achieved anything significant at the Slam, where he has since exited in the second round twice, reached the third round once and been eliminated in the last 16.

Notably, his run to the fourth round came last year after missing the tournament in 2022, 2023 and 2024, and it remains to be seen which version of the veteran turns up on Monday.

That feeling of uncertainty is compounded by a mixed grass season, where he reached the quarter-finals at the Libema Open — losing to Monday's opponent — before an early exit to Ugo Humbert at Queen's last week.

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Yet, the player on the other side of the net has his own eccentricities, and it remains to be seen whether we get good Daniil or bad Daniil in the opening round.

Medvedev entered the 2025 Championships on the back of consecutive semi-final runs, only to fall to Bonzi in his first match.

That loss followed his tournament-opening exit to Cameron Norrie at the French Open, and more disappointment in Flushing, where he was beaten by Bonzi again in the first round.

While that unwanted streak of first-round defeats was halted in Australia in January, where he reached the fourth round, Medevev heads into his eighth appearance at SW19 after another early exit at Roland Garros, although taking into consideration his love-hate relationship with the clay.

Nonetheless, a pair of strong grass season runs have seen the former world No. 1 reach the semi-finals in 's-Hertogenbosch before reaching the last-eight in Halle.

As such, the 30-year-old's momentum appears to be better ahead of a sixth meeting with Cilic, but with Medvedev, you can never be so certain.

Head To Head

's-Hertogenbosch (2026) - Quarter-final: Medvedev 6-2 3-6 6-1

French Open (2022) - Fourth round: Cilic 6-2 6-3 6-2

Davis Cup Finals (2021) - Final: Medvedev 7-6(7) 6-2

Wimbledon (2021) - Third round: Medvedev 6-7(3) 3-6 6-3 6-3 6-2

Washington (2019) - Quarter-final: Medvedev 6-4 7-6(7)

Medvedev leads Cilic 4-1 in their ATP Tour head-to-head, with the Russian targeting another grass-court victory over the veteran after this month's win in Den Bosch.

The Libema Open clash was their first meeting since the 2022 French Open fourth round, when the Croat prevailed in straight sets.

While Medvedev leads 2-0 in their grass-court contests at Wimbledon (2021) and 's-Hertogenbosch (2026), both matches have gone the distance.

The former world No. 1 roared back from two sets down to defeat Cilic at SW19 five years ago and recovered from dropping the second set in Den Bosch to clinch the decider. 

We say: Medvedev to win in four sets

On the one hand, one is inclined to back Medvedev for comfortable success against Cilic, especially given his superior form ahead of the third Slam of the year.

However, the former world No 1 can be unpredictable, meaning a confident punt on him leaves you exposed.

Considering previous meetings on grass have been tight affairs, Cilic picking up one set or two cannot be ruled out.

Nonetheless, Medvedev is tipped to edge Monday's meeting in four tight sets to advance to the second round.