Since Novak Djokovic first lifted the Wimbledon trophy in 2011, Centre Court has felt like his second home. And now, at 38, he’s back in the semi-finals, this time not just to chase history, but to send a message. After grinding out a four-set win over Italy’s Flavio Cobolli, Djokovic advanced to his 14th Wimbledon semi-final and 52nd Grand Slam semi-final overall. But it wasn’t just the numbers that stood out; it was the message behind them.

With a sly smile, Djokovic teased, “You want numbers?” before letting the stat speak for itself. The numbers are mind-boggling, but it’s his presence and purpose that remind everyone, including World No. 1 Jannik Sinner, that Djokovic isn’t clinging to relevance. But after the victory over Cobolli, when Djokovic was asked about how much this moment means to him. Djokovic’s response came with honesty and heart. “Wimbledon… it was, is, and still remains and always will be the most special,” he said. “It means the world to me that I’m still, you know, still able at 38 to play the final stages of Wimbledon… it’s beautiful. Makes me feel very young.”

Well, Djokovic has just made history once again, reaching a record 14 Wimbledon semi-finals and his 52nd Grand Slam semi-final. He is still hunting his 25th major at the age of 38, and that itself says a lot. However, it is not merely the statistics. Each match that he wins, in particular those coming against the younger generation of players, as he has done against Flavio Cobolli and now awaits Jannik Sinner, he is sending a very clear message that experience and years of playing and competing at the highest level do matter. But with this, he showed age is nothing but a matter of when your wins get counted.

Then came Djokovic’s charm, light but loaded. “Another thing that makes me feel very young is competing with youngsters, you know, like Cobolli today.” He wasn’t done. “I enjoy kind of sliding and running around the courts with him and with all the other guys. Speaking of all the young guys, you know, I’m going to have one in the next round. So I look forward to that. That’s going to be a great, great matchup.” It wasn’t trash talk; it was Novak being Novak. Honest. Calm. Deadly. And sending an indirect message to Jannik as well.

So here we are: Sinner vs. Djokovic in a semifinal with all the stakes in place. One is a 23-year-old, ranked top Italian who happens to be peaking at the right time. The other, who is 24-times a Grand Slam champion and is here so many times it almost looks like cheating. However, don’t get it wrong; Djokovic is not playing on a reputation; rather, he is playing with a point. He is familiar with the doubts; he listens to the gossip about age, but he still responds with faith. “Thank you for choosing me… at my age. I appreciate it,” he said, smiling. Experience may not trend, but it wins. And Djokovic isn’t done winning just yet. Game on. So, who do you think takes this one? The past favors Sinner, but the current form? That’s still up for debate.

Youth has the stats, but Novak Djokovic has the stage

Well, so much for age being a disadvantage. Novak Djokovic clearly proved that 38 years of age is nothing when you are Novak after he demolished 23-year-old Flavio Cobolli at Wimbledon. Seven-time winner played a bit unstable in the early part of the game as he lost the first set by tiebreak, but when he began to find his game, there was nothing anyone could do. He beat Cobolli 6–7(6), 6–2, 7–5, 6–4 in a match that had it all: moments of magic, a brief injury scare when Djokovic fell on match point, and that trademark coolness under pressure. But on his third match point, Novak was through to yet another Wimbledon semifinal. And now?

We’re getting Djokovic vs. Sinner, Round 10. Yes, that Sinner. The world number one. The man who beat Novak at this exact stage last year. Their head-to-head stands at 5–4 in Sinner’s favor, with Grand Slams split evenly at 2–2. But it’s Sinner who’s won three of their last four completed matches, including a straight-sets stunner in the 2025 French Open semifinals just last month. If you’re counting, that’s three wins on three different surfaces for the Italian over the last year. Advantage Sinner? Maybe. But with Novak, it’s never that simple.

Let’s talk receipts. Djokovic schooled a young Sinner in their first clash back in Monte Carlo in 2021. He followed it up with a signature comeback at Wimbledon 2022, rallying from two sets down in vintage fashion, and again dominated at the 2023 Wimbledon semifinal. But the tides have shifted. Sinner claimed his first win in the 2023 ATP Finals group stage, then beat Djokovic again in the 2023 Davis Cup semis, followed by powerful performances at the 2024 Australian Open and the Shanghai final. The Italian also stunned Djokovic at Roland Garros 2025 in straight sets and has taken five of their last eight completed matches. But this Friday, there’ll be no excuses. Just grass, legacy, and fire. Can the king of Centre Court reclaim his crown, or will the future finally shut the door on the past? Only time will tell. Stay locked in with minute-by-minute coverage on EssentiallySports’ live blog of The Championships.