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Djokovic Outdoes Federer, Advances to 14th Wimbledon Semifinal

Will the Serbian tennis legend who lost Roland Garros to World No. 1 Jannik Sinner beat him this time for a 25th Grand Slam?

By Rudra Mulmule | LAST UPDATED: JUL 10, 2025

There are moments in sport when time folds in on itself. The crowd leans forward, the grass seems greener, and the weight of history hangs not just on the scoreboard, but in the stillness between points. Novak Djokovic, who played a tough quarter finals against the number 22, Flavio Cobolli, gave us one of those moments at Wimbledon last night.

In what has become a near-annual tradition, the 38-year-old Serbian maestro carved out yet another corner of tennis history, stepping into the semi-finals at SW19 for a record-breaking 14th time — eclipsing Roger Federer’s previously untouchable mark of 13.

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A still of Italian player Flavio Cobolli and Novak Djokovic shaking hands post the quarter final game at Wimbledon.Instagram/djokernole

The numbers alone are staggering, but for those who have followed Djokovic's career closely, know that this feels less like a final act and more like the third encore of a performer who simply refuses to leave the stage.

In a gripping four-set encounter on Centre Court, Djokovic dispatched Italy’s Flavio Cobolli 6-7 (6-8), 6-2, 7-5, 6-4 — a scoreline that only partially reflects the tactical precision and mental tenacity on display. It was a match defined by resilience and experience on Djokovic's part and defiance to give up from the young Italian tennis player, Cobolli. Ultimately, making us glued to our seats till the very last shot. And a unanimous gasp in the fourth set when Djokovic almost injured himself.

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Djokovic's quarter final win is special more than any others. This is not only his 52nd time at the Grand Slams, the Serbian player has officially made history yesterday tying with the great Chris Evert for the most in tennis history (men or women). But the record breaking doesn't end here.

Djokovic has become the second-oldest man ever to reach the semi-final in London (just behind Ken Rosewall) and here's the best part: he is the third person to do this at the age 38. But this may not be the only records he might be making this year.

Novak Djokovic; tennis; wimbledon; sports; racquet sports; lawn tennis; grand slam; all english club; uk;
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Now, awaiting him in the semi-finals is World No. 1 Jannik Sinner, the 23-year-old Italian phenom who recently bested Djokovic at Roland-Garros. If he beats Sinner at the semi-finals this week, he'll be competing for his 25th Grand Slam. Or it'd be a moment when of passing of the torch? Perhaps. But not yet.

Djokovic has played more semi-finals than Federer. More majors than Serena. A career so complete it now functions as a mirror, reflecting back the greatness of every era he has outlasted.

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What’s Next

Friday's semi-final against Sinner promises a stylistic contrast: youth vs experience, rhythm vs reaction. Win or lose, Djokovic’s pursuit of a 25th Grand Slam continues to bend the physics of possibility.

Novak Djokovic; tennis; wimbledon; sports; racquet sports; lawn tennis; grand slam; all english club; uk;
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But more than just chasing titles, Djokovic is now redefining longevity in tennis. He’s turning the sunset of a career into its own kind of spectacle and not fading into the twilight but running, sliding, and shouting his way through it.