Preview: Wimbledon: Alex de Minaur vs. Flavio Cobolli - prediction, head-to-head, tournament so far

Flavio Cobolli will hope to be third-time lucky against Alex de Minaur on Monday, when both top-10 players face off in the fourth round of Wimbledon for a place in the quarter-finals.

Despite his little competitive action on the grass, Cobolli has picked up his Grand Slam run where he left off, having reached the Roland Garros final, but he faces an opponent he has never defeated and one having a fine run on the surface this year.

Match preview

Sometimes, a positive run in the tournaments leading up to a Grand Slam never translates into a deep run at the leading events, but De Minaur has avoided that trap.

The Demon reached the title match at the Libema Open last month, before following it up by reaching the quarter-finals in Queen's, where Brandon Nakashima beat him.

However, he has responded to that mini-setback by notching three consecutive wins at the All England Club, where he is a one-time quarter-finalist, after making the last eight in 2024.

Although he could not match that performance 12 months ago, falling to Novak Djokovic in four sets, the world No. 6 returns to the last 16 at the Championships seeking to right the wrongs of 2025's fourth-round exit.

Entering his third meeting with Cobolli holding an 8-2 record on grass this season, the 27-year-old will back himself for a ninth grass-court success to advance to the quarter-final.

Facing his Italian opponent poses a different challenge, especially after the ninth seed's recent run to the title match in Paris.

Even though grass presents its unique tests, Cobolli now knows what it takes to go deep in a Grand Slam, undeniably standing him in good stead.

The world No 10's belief probably grew after last year's run to the last eight at SW19, having previously not gone beyond the third round of a Major before surging to the last eight at the Championships.

This year's challenge has been acclimating to the surface shortly after facing Alexander Zverev in the Paris decider, with his only pre-Wimbledon appearance ending early at the hands of Frances Tiafoe in Halle.

Perhaps that explains the Italian needing to battle through in every round, needing to win two tiebreaks in his comeback first-round win over Mariano Navone, doing likewise against James Duckworth in his second match and recovering from an opening-set bagel and trailing two sets to one to beat Karen Khachanov in five.

Fresh off Saturday's Karen Khachanov 0-6, 7-6(4), 6-7(5), 6-2, 6-2 third-round success, Cobolli seeks another to match last year's admirable performance ahead of a possible quarter-final match against resurgent Grigor Dimitrov or home wild card Arthur Fery.

Tournament so far

Alex de Minaur:

First round: vs. Roman Andres Burruchaga 7-6(5) 6-1 6-0

Second round: vs. Adrian Mannarino 6-3 6-2 6-2

Third round: vs. Zachary Svajda 6-2 5-7 6-2 6-4

Flavio Cobolli:

First round: vs. Mariano Navone 1-6 7-6(5) 6-3 7-6(8)

Second round: vs. James Duckworth 7-6(4) 3-6 7-6(3) 6-1

Third round: vs. Karen Khachanov 0-6 7-6(4) 6-7(5) 6-2 6-2

Head To Head

Vienna Open (2024) - Round of 16: De Minaur 7-6(2) 3-1 ret.

Australian Open (2024) - Third round: De Minaur 6-3 6-3 6-1

Although De Minaur leads Cobolli 2-0 in their head-to-head, Monday's match will mark their first grass-court meeting on the ATP Tour.

The Demon's wins came on home turf at the 2024 Australian Open before securing another success over the Italian in indoor conditions in Vienna later that year.

Still, Cobolli's level has grown since those two matches, with the 24-year-old now a three-time ATP champion, having also claimed four top-10 wins since the start of 2025, albeit all have come on clay.