The Wimbledon quarterfinal between Novak Djokovic and Flavio Cobolli was billed as a clash of generations—an aging legend with 24 Grand Slam titles to his name versus a fearless newcomer making his first major quarterfinal appearance. What unfolded under the Centre Court roof was a spectacle that went well beyond the scoreboard. One that had the crowd perhaps too excited!

With a 25th major and a record-extending eighth Wimbledon crown in sight, the Serbian maestro stepped onto the court to face Cobolli, a 23-year-old Italian who, once upon a time, “hated grass.” That disdain is now ancient history. Cobolli’s run to the quarters was fearless, full of fire and fizz.

With Hollywood royalty like Hugh Grant in the stands and Italian flair from Fabio Fognini in attendance, Centre Court was electric. Unfazed by the occasion or his childhood icon across the net, the Italian took the first set in a tiebreak, breaking Novak Djokovic with bold baseline winners and timely aces. As the match wore on, Djokovic dialed up his first serve and began to target Cobolli’s second, taking the second set 6-2. The third set ratcheted the tension even higher. Cobolli produced a remarkable 20-minute stretch of relentless hitting to surge ahead, only to get caught flat in a pivotal 5–5 game that handed Djokovic a crucial break. The seven-time champion closed it out 7–5, his unwavering experience proving decisive. But it wasn’t just Cobolli across the net; Djokovic had another familiar opponent: the crowd.

Even when the cheers were for him, Djokovic seemed irked. In the fourth set, as the match tightened and tension pulsed through the arena, he turned to the crowd and repeatedly brought a finger to his lips. Shushing fans who, ironically, were on his side. The chair umpire eventually stepped in, urging the crowd to maintain silence during serves.

His hot and cold relationship with crowds isn’t new. During his fourth-round match against Holger Rune at Wimbledon last year, the tension was on full display. Hundreds of fans greeted Rune’s winners and Djokovic’s errors with stretched-out cries of “Ruuuuuuune,” a chant the Serb took as disrespect. After winning, when on-court interviewer Rishi Persad suggested the crowd was simply backing his opponent, Djokovic didn’t buy that explanation and said he knew all the “tricks.” 

Djokovic won over both opponents. The 24-time Grand Slam champion did what he does best: win! After failing to convert the first match point, he slipped on the baseline during the second point. However, he returned to his feet soon after and eventually finished the job to reach the semifinals of SW19.

And as you know, every Novak Djokovic victory creates some history.

Novak Djokovic breaks Roger Federer’s record with quarterfinal win

Now chasing an eighth Wimbledon crown to match Roger Federer’s record, Novak Djokovic has already etched his name into history in another way. By reaching his 14th semifinal at the All England Club on Wednesday, he passed Roger Federer for the most among men in the Open Era.

It’s also his seventh straight semifinal appearance at Wimbledon, tying Federer’s streak from 2003 to 2009. One more win would take him to a third consecutive final, but standing in his way is World No. 1 Jannik Sinner.

Sinner, who ended Ben Shelton’s run with a 7-6(2), 6-4, 6-4 victory, leads Djokovic 5-4 in their ATP Head2Head series. The Italian also beat Djokovic in the Roland Garros semifinal last month. But the Serb holds the edge at Wimbledon, having defeated Sinner at SW19 in both 2022 and 2023.

Through cheers and boos, Novak Djokovic keeps winning. Now the question is, can he finally lift Grand Slam No. 25? Follow the Championships in real-time with EssentiallySports’ Live Blog updates.