The first time Novak Djokovic stood up and took notice of Jannik Sinner’s burgeoning talent was on the grass of the All England Club three years ago. The Italian, then just 20, stormed to a two-set lead in their quarter-final on Centre Court. Djokovic, aware of the severity of the situation, headed to the bathroom underneath the Royal Box.
“I had a refresh, a toilet break, and a little pep talk to myself in the mirror,” he would say afterwards. “That’s the truth.” Djokovic would go on to claim victory in five, with a spectacular backhand cross-court winner leaving him flat on his chest, the money-shot moment of the match.
Djokovic also defeated Sinner in the 2023 semi-finals in an impressive straight-sets victory. But this, indisputably, is a different scenario some two years on. And as the two square off once more – five weeks on from the same match-up, in the same slot, at the same round of the French Open – it is the world’s best player in Sinner who boasts a fearsome record against the Serb.
The 23-year-old, 15 years younger than Djokovic, has won their last four meetings and the last six sets in a row. The Serb, the greatest men’s player to ever play the game, has not beaten Sinner in 30 months. It is a daunting prospect, as the duo face off again in their blockbuster last-four clash on Friday afternoon.
Daunting, but not insurmountable.
“I lost in straight sets to Jannik in the semis of Roland Garros, I think I played a solid match,” Djokovic said, after his four-set win against Flavio Cobolli in the quarter-finals on Wednesday.
“I could have played better, but he was just the better player when the moments were important. So, I get another opportunity. Hopefully, I can deliver the level and I’m able to stay with him for potentially five sets.
“It’s going to take the best of me at the moment to beat Jannik. I mean, I know that.”
The key difference between this occasion and the Paris squabble last month is, rather obviously, the surface beneath their feet.
While Sinner has the upper hand on hard and clay, he has never defeated Djokovic on grass. And we have already seen the world No 1 on the receiving end of an almighty reprieve this year, given his two-set deficit to Grigor Dimitrov in the fourth round, before the Bulgarian had to agonisingly retire.
Simply put, it makes Sinner vulnerable. The nuances of grass-court movement, the slipping and sliding on the edges of the court as the tournament progresses, are a delicate art. It is one which Djokovic has mastered over his 20-year career, ahead of his 14th Wimbledon semi-final.
Add to the equation that the Italian is nursing an elbow injury obtained against Dimitrov, and it makes him beatable. That being said, it remains to be seen how Djokovic himself will recover from his late fall against Cobolli, with the Serb cancelling his practice session on Thursday. But if past powers of recovery are anything to go by, Djokovic will be fit and fighting.
“Me and Novak, we know each other better because we played quite a lot,” said Sinner, after his quarter-final win against Ben Shelton. “So we understand what’s working and what’s not.
“But yeah, I’ve never won against him here in Wimbledon.”
There is another element to this, which goes back to Sinner’s three-month drugs ban earlier this season; a suspension, timed conveniently, which resulted in him not missing a major. It’s not common for Djokovic to be backed fully by the Centre Court crowd, but Friday could have a different feel.
It’s likely that the winner will face Carlos Alcaraz, with the defending champion an overwhelming favourite against world No 5 Taylor Fritz from the United States in the first semi-final. The Spaniard’s last two finals here, against Djokovic, have been riveting affairs. But, given that final in Roland Garros against Sinner, Wimbledon will want a slice of the next big rivalry in men’s tennis.
Intriguingly, a Sinner-Alcaraz repeat would be the first time the men’s finals at Roland Garros and Wimbledon have matched in the same year since Roger Federer and Rafael Nadal in 2008.
Yet for Djokovic, who broke through and bettered the records of those two legends, the next few days represent his best chance at claiming a record-breaking 25th grand slam – and with it becoming the oldest singles major winner in history. He admitted pre-tournament he was unsure if this would be his “last dance” at SW19.
All the odds seem stacked against him. But it is in these scenarios that Djokovic has thrived, time and again, throughout his storied career.
Sinner is eyeing a first Wimbledon final and the inevitable pressure that comes with that. Much like most latter-round contests at grand slam level, it will come down to fine margins but, unlike Paris, perhaps Djokovic holds the upper hand in this regard, where his well-crafted range of shots in the face of Sinner’s bludgeoning groundstrokes should be more effective on grass.
Djokovic’s variety is his key weapon. While his wide array of shot-making was gobbled up delightfully by Sinner five weeks ago, on the checks and flat-lining of the grass, it is a different proposition altogether.
But the underlying sentiment persists, too, that it could be Djokovic’s last chance saloon. Can the Serb – the king of big moments in big matches – come up with the goods one final time? We should be in for a cracker.
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