What Happened to Novak Djokovic Last Time He Faced Jannik Sinner in Semi-Finals? Everything You Need to Know Ahead of Wimbledon Clash

Novak Djokovic is ready for another battle! After reaching his 14th Wimbledon semi-final, the seven-time champion will face his rival and World No.1, Jannik Sinner. This clash surprisingly echoes their 2023 semi-final showdown on these very courts. While Nole has struggled against the fiery Italian, will this time be different? Let’s find out!

Back in 2023, the Wimbledon semi-final stage was set for a clash like no other. Sinner, making his first-ever semi-final, faced Djokovic, who was chasing a fifth straight Wimbledon final. Djokovic put on a classy, all-around show to win 6-3, 6-4, 7-6(4), marking his 34th straight grass-court major win. But it wasn’t easy. The 21-year-old Italian eighth seed had pushed Nole to the brink the previous year, coming back from two sets down before Djokovic finally prevailed.

This time, the Serb took early control, cruising through the first set and breaking in the second. But tensions flared when umpire Richard Haigh docked Djokovic a point for a distracting noise and later warned him for slow serving—prompting a fiery “what are you doing?” from Novak.

Tennis – Wimbledon – All England Lawn Tennis and Croquet Club, London, Britain – July 5, 2022 Serbia’s Novak Djokovic reacts during his quarter final match against Italy’s Jannik Sinner REUTERS/Toby Melville

Still, Novak Djokovic kept his cool, ruthlessly winning the second set. After saving two set points in the third, he cheekily responded to the crowd cheering for Sinner with a sarcastic crying gesture. In the end, Djokovic had the last laugh, clinching the tie-break and moving closer to history.

But now? Things have changed. They’ve met six times since, with Jannik Sinner winning five. Novak’s last win was at the 2023 ATP Finals, where he took the title. Yet in their last three clashes, the Italian has dominated. He even stopped Novak’s run at the 2025 French Open semifinals, cutting short his quest for a 25th title and fourth Roland Garros crown.

Right now, both players have shown grit and determination to make it into the semifinals. Albeit they’ve both sustained injuries in their previous matches, which might cause a slight hindrance. So, what can we expect from them now?

Novak Djokovic’s chances against Jannik Sinner

Djokovic’s journey to the Wimbledon semis wasn’t exactly smooth sailing. He dropped a set to Flavio Cobolli and Novak took a “nasty fall” in the fourth set that had everyone gasping. Leading 40-30, Novak’s leg got stuck in the grass as he lunged for a shot, sending him crashing to the court in pain. After lying there for several seconds, he bounced back up and finished the match. “I’ve had quite a few of those throughout my grass court career, but obviously, body is not the same today like it was before. So, I guess the impact of what happened I will feel tomorrow,” Djokovic said, adding he’d get the injury checked by the physio.

Jannik Sinner’s Wimbledon run has been nothing short of spectacular. Before facing Grigor Dimitrov in the Round of 16, the World No. 1 hadn’t dropped a set. But that match took a wild turn. Dimitrov’s right arm injury helped Sinner advance despite losing the first two sets. Yet, the match took a toll on Jannik too—he slipped on the grass and landed hard on his right arm, causing sharp elbow pain. On his day off, Sinner got an MRI and kept training indoors with coaches Simone Vagnozzi and Darren Cahill.

After beating Ben Shelton in the quarters, he revealed how he managed the pain: “Yeah, I mean, when you are in a match with a lot of tension, you try not to think about it. It has improved a lot since yesterday to today. Yesterday, my day was very short on the practice court—20 minutes with the coaches only. But in the other way, I’m looking forward to it. It’s no excuse, so there is no better stage to play tennis, and I think I showed this today.” But is he ready to take on Nole? The Serb seems quite ready!

After his win over Cobolli, Novak Djokovic was asked what this moment means to him. His answer was heartfelt: “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.” At 38, Djokovic has just made history again, reaching a record 14th Wimbledon semi-final and his 52nd Grand Slam semi-final. Still chasing his 25th major, Novak’s hunger is as fierce as ever.

Now, can Djokovic take on Sinner in their 10th clash? The Italian has won their last three meetings, including the 2025 French Open semis, but there’s a lot at stake for Novak here. A win would send him to his 11th Wimbledon final, where he’d face the winner of today’s semis between Carlos Alcaraz and Taylor Fritz.

Alcaraz, with an 8th Grand Slam semi-final appearance and a stellar 34-3 grass record, is a strong favorite. Fritz, fresh off a dominant quarterfinal win over Khachanov and riding the momentum of his 2024 US Open runner-up run, is no pushover. Their head-to-head favors Alcaraz 2-0, but can Fritz pull off a shock in his first Wimbledon semi? Only time will tell. Stay updated with real-time coverage of the Championships, only on EssentiallySports Live Blog!

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