Novak Djokovic vs. Jannik Sinner: a blossoming cross-generational rivalry?

Last November, Novak Djokovic and Jannik Sinner crossed paths three times over a 12-day stretch on a match court. The Italian won two of the three meetings in making headway in his head-to-head series with the storied champion, though watched Djokovic lift a record-breaking seventh Nitto ATP Finals trophy in their Turin final rematch.

On Tuesday, both won their respective quarterfinal matches at the Australian Open to set a highly-anticipated pre-tournament projected semifinal In Melbourne. After Djokovic defeated Taylor Fritz in four sets, Sinner handed Andrey Rublev his 10th defeat in 10 major quarterfinals to reach the last four without dropping a set.

“This is what I practice for, no, to play against the best players in the world. Obviously (Novak) has an incredible record here, so for me it's a pleasure to play against him, especially in the final stages of the tournament where things are a little bit more interesting,” Sinner said after equaling his best major showing.

Three days later, the Italian became the first player to ever knock out Djokovic at this juncture of the tournament to move within a victory of joining the major winner's club.

A look at their past meetings in what looks to be a budding cross-generational rivalry:

2021 Monte Carlo R32 (Djokovic)

Djokovic brought the pressure in their first encounter by winning more than half of the points played on Sinner’s first serve. It resulted in breaking the then 22nd-ranked Italian five times en route to posting a comfortable victory in the second round, Djokovic’s opening match of the Masters 1000 event. The veteran had nothing but good things to say about Sinner’s future afterwards.

“He really has a good mindset. He seems more mature for his age than the rest of the guys with the way he's playing and training. He's got a good tempo. From the baseline he makes the other guy feel he's got to run a lot. I like his game.”

2022 Wimbledon QF (Djokovic)

Having taken out Carlos Alcaraz in the round of 16, Sinner arrived to his first Wimbledon quarterfinal full of confidence. And it showed when he jumped out with the first two sets against the top seed on Centre Court. Djokovic however, stepped up his game in a big way. Over the next three sets, he went 17/20, 17/18 and 12/12 on his first serve in showing once again just how difficult he is to close out in best of five.

“I always believed that I could come back. I know the experience I have could eventually prevail in these kind of situations,” he said.

2023 Wimbledon SF (Djokovic)

Going a step further to make his major semifinal debut, Sinner’s hopes of a significant breakthrough moment were virtually dashed from the start. After missing two chances to break in the opening game, Sinner dropped his first service game to immediately find himself playing from behind. Djokovic would add a further blow when he saved a pair of set points in the 10^th game of the third set, before winning the final four points of the tie-break.

“Each set was closer than it appears maybe on the scoreboard. I knew that he is going to try to be aggressive and hit from both forehand and backhand quite flat and fast, so I needed to be really sharp from the beginning, which I think I have,” Djokovic assessed.

2023 Nitto ATP Finals – Round Robin (Sinner)

Playing with a home crowd advantage, an inspired Sinner found a new gear to score his first win over Djokovic. He came in with plenty of form that included a pair of ATP 500 titles in October. Two points from losing, Djokovic leveled by winning a crucial second-set tiebreaker. Sinner then showed his resolve when he bounced back from seeing a 4-2 advantage in the final set go to waste by claiming the first five points of the decisive 'breaker.

“With the crowd and everything, they are trying to really help me. I'm obviously very happy how I tried to put everything in the right direction,” the local hero said.

2023 Nitto ATP Finals – Title Match (Djokovic)

It’s hard enough to beat Djokovic once. But twice in the same tournament? Sinner knows. The world No. 1 exacted his Turin revenge in impeccable fashion in becoming the most decorated champion in tournament history. How did he do it? By channeling his inner serve bot: 13 aces, zero double faults and just seven points conceded at the line later, Djokovic completed a comprehensive performance when his opponent double-faulted to end it.

“It's a great reward I think for what my team and I and my family have been through this year, being one of the most successful years in my career that I ever had. Four out of five major tournaments I won, played finals of Wimbledon. I couldn't ask for more, to be honest. I'm very, very proud of the season,” reflected the 24-time major title holder.

2023 Davis Cup Finals – SF Tie (Sinner)

Throughout his career, Djokovic has pulled off more than his fair share of improbable comebacks. On this day however, he was on the receiving end of one. After hitting back to trade 6-2 sets with the 22-year-old, Djokovic opened a 0-40 lead with Sinner serving at 4-5 in their decider. Of Djokovic's three missed match points, the first one stung the most when he floated a backhand slice long during a neutral rally. Sinner then hit his spots on a strong series of serves to keep the revered returner at bay—finishing with an ace down the T—and went on to capture the final three games to keep his squad alive. Sinner then beat Djokovic on the doubles court (alongside Lorenzo Sonego) to send Italy into the championship tie, and capped off a perfect week the following day by clinching his nation's first Davis Cup crown since 1976.

“Match of my life? I don't know. But it's for sure very important,” Sinner would tell the Davis Cup website.

2024 Australian Open SF (Sinner)

Djokovic is widely regarded as the greatest returner of his generation, if not all-time in men's tennis. It makes what Sinner managed to accomplish in their first Aussie Open encounter all the more remarkable. For the first time in his career, Djokovic did not create a break point opportunity in a completed Grand Slam match (h/t Tennis Abstract). He dug in to force a fourth set after saving a match point, but Sinner would not be denied his first Grand Slam final appearance in an effort that saw the No. 4 seed win 30 more points than his counterpart.

“I realized, especially the first sets, he was not playing that great, but I tried to have the intensity as high as possible, and I took the chance,” Sinner said.