Preview: Wimbledon: Flavio Cobolli vs. Novak Djokovic - prediction, head-to-head, tournament so far

First-time Grand Slam quarter-finalist Flavio Cobolli will face his idol and 16-time Wimbledon quarter-finalist Novak Djokovic in Wednesday's last-eight contest, aiming for an upset to reach the semi-finals.

The Italian was emotional after defeating veteran Marin Cilic in Tuesday's fourth round, setting up a second encounter with Djokovic on the ATP Tour after last year's match in Shanghai.

Match preview

The joy on Cobolli’s face was unmistakable after a thrilling victory over Cilic in four tight sets to reach his first Grand Slam quarter-final.

Completed in three hours and 25 minutes, the 23-year-old has advanced to the last eight at SW19 in just his second main draw appearance, having exited in the second round 12 months ago.

The reward for overcoming a veteran who served 19 aces is a clash with a seven-time Wimbledon champion and 24-time Grand Slam winner, whom he faces for the second time on the men's tour.

Cobolli has previously mentioned his veneration for the Serbian, revealing that the 100-time ATP champion is his idol, but he must set feelings of admiration aside in hopes of an upset victory.

Such an outcome will require the Italian to elevate his game significantly from their previous meeting in Shanghai last year, which Djokovic won in straight sets.

If the No. 22 seed is to pull off the upset against the 38-year-old, he will need a dip in form from the sport's greatest player, who struggled in his opening set against Alex de Minaur before recovering to defeat the Australian in four.

Having served at an exceptionally high level in rounds one, two and three — winning free points with 22 aces against Alexandre Muller, 11 against Dan Evans and 16 against countryman Miomir Kecmanovic — the sixth seed only managed six against De Minaur, who broke his serve six times on Monday, five more than in the previous rounds.

Despite the challenge, saving break points down 4-1 in the fourth and winning the next five games meant Djokovic avoided a fifth-set decider, securing his spot in a 16th quarter-final at the All England Club with a 1-6, 6-4, 6-4, 6-4 victory.

Djokovic, now 101-12 at Wimbledon after Monday's win, remains the favourite to progress to another semi-final, where Jannik Sinner or Ben Shelton await.

Fresh off defeating a 29th top-20 opponent at Wimbledon — only Roger Federer (32) has more — the seven-time champion, who has reached the last six finals at SW19, is expected to avoid his earliest exit since 2017's quarter-final loss to Tomas Berdych and compete in Thursday's semi-final.

Tournament so far

Flavio Cobolli:

First round: vs. Beibit Zhukayev 6-3 7-6(7) 6-1

Second round: vs. Jack Pinnington Jones 6-1 7-6(6) 6-2

Third round: vs. Jakub Mensik 6-2 6-4 6-2

Fourth round: vs. Marin Cilicc 6-4 6-4 6-7(4) 7-6(3)

Novak Djokovic:

First round: vs. Alexandre Muller 6-1 6-7(7) 6-2 6-2

Second round: vs. Dan Evans 6-3 6-2 6-0

Third round: vs. Miomir Kecmanovic 6-3 6-0 6-4

Fourth round: vs. Alex de Minaur 1-6 6-4 6-4 6-4

Head To Head

Shanghai Masters (2024) - Round of 32: Novak Djokovic 6-1 6-2

Cobolli will hope for a markedly better performance against his idol when they meet for the second time on the men’s tour.

They previously faced last year in Shanghai, where Djokovic secured a comfortable straight-sets win en route to reaching the final at the Masters, ultimately falling to Jannik Sinner.

While the 23-year-old first-time quarter-finalist aims for an upset in their second encounter, his 1-11 record against top-10 opponents shows there is quite a way to go before challenging the sport’s elite.

We say: Djokovic to win in three sets

To beat Djokovic on Centre Court, Cobolli will need to play the match of his life and hope for another underwhelming display from the seven-time champion to reach his first semi-final at a Major.

Considering the circumstances, the Serbian player, unlikely to be as underwhelming as against De Minaur, is favoured to advance to yet another Wimbledon semi-final.

Previews by email