Novak Djokovic’s quest for tennis history continues on Wednesday at Wimbledon’s Centre Court, where the seven-time champion and sixth seed meets Flavio Cobolli, a 23-year-old Italian newcomer making his Grand Slam quarterfinal debut.
Djokovic, 38, is chasing a record-equaling eighth Wimbledon title and an unprecedented 25th major singles crown.
After a shaky start against 11th-seeded Alex de Minaur in the fourth round, the Serbian recovered to win in four sets, advancing to his 16th Wimbledon quarterfinal, second only to Roger Federer.
Despite the pressure, Djokovic remains composed, leaning on two decades of elite-level experience and a 99-10 career record at Wimbledon.
Cobolli, ranked No. 24, enters the biggest match of his life with nothing to lose.
A former junior footballer with AS Roma, he has turned heads with a fearless run, defeating veterans and rising talents alike.
His four-set win over 2014 US Open champion Marin Cilic in the last round confirmed his credentials: powerful baseline play, composure under pressure, and a shot-making flair that’s delighted crowds and stunned seeded opponents.
Djokovic’s path to the quarters has not been without turbulence. After dropping a set in his opener, he breezed past Dan Evans and Miomir Kecmanovic before encountering serious resistance from De Minaur. Down a set and 4-1 in the fourth, he flipped the script with a vintage comeback to win 1-6, 6-4, 6-4, 6-4.
His 13.8 aces per match and nearly 79% first-serve win rate have been vital, though an uptick in double faults has raised concern.
Cobolli’s campaign has been clean and composed. He dropped his first set of the tournament against Cilic but held firm in the tiebreak to secure a 6-4, 6-4, 6-7(4), 7-6(3) victory in over three hours.
The win was emotional – his father and coach Stefano shedding tears courtside – as Cobolli became the first Italian man since Berrettini in 2021 to reach the Wimbledon quarters.
The two met once before – at the 2024 Shanghai Masters – where Djokovic cruised 6-1, 6-2.
That memory lingers, but Wimbledon’s grass and the stage’s gravity offer a different script.
Cobolli has matured, winning titles in Bucharest and Hamburg this season and reaching the Halle quarterfinals.
Despite a first-round exit in Eastbourne, his game has translated surprisingly well to grass, a surface he once claimed to “hate.”
Djokovic, known for thriving under pressure, holds all the statistical edges: 63 Grand Slam quarterfinals to Cobolli’s 63 career ATP Tour wins, an 89% Wimbledon win rate, and unmatched mental resilience. Yet his fourth-round scare, recent surgery recovery, and signs of wear could offer Cobolli a window, particularly if Djokovic starts slow again.
Cobolli’s hopes lie in unpredictability: injecting variety, slicing and dropping, keeping rallies short, and forcing Djokovic off rhythm.
But he’ll need to serve well and avoid lapses. Djokovic, likely to pin him to the baseline and probe for errors, will look to close quickly and conserve energy for deeper rounds.
Weather conditions – mild with light wind – may favor consistent ball-striking, but any shift could unsettle rhythm, particularly for Djokovic, who struggled in swirling wind against De Minaur.
Should Djokovic win, a tantalizing semifinal against world No. 1 Jannik Sinner may await. For Cobolli, win or lose, this Wimbledon run has announced his arrival among tennis’s next wave.
