When the Wimbledon draw was made, one of the big questions was where Novak Djokovic would land. Would the seven-time champion fall in World No. 1 Jannik Sinner’s quarter or half, or would the Serbian end up only having the chance to meet the Italian for the title?
When it turned out they could clash in the semi-finals, there was still a long way for both men to reach that point, especially given Sinner’s shock second-round Roland Garros exit and Djokovic’s grueling third-round upset at the hands of Joao Fonseca in Paris. But with 28 major titles between them — 24 for Djokovic and four for Sinner — there was always a high chance that the tournament favourites would navigate their way through the field.
Although neither man has quite found imperious form this fortnight — Sinner fell behind two sets to one in his first match of the tournament against Miomir Kecmanovic, while Djokovic needed four sets in three of the first four rounds before battling past Felix Auger-Aliassime in a classic five-set tussle — they now stand ready for what promises to be a classic duel in the semi-finals Friday.
For the fourth time in five years, two of the biggest icons in the sport will play one another at Wimbledon. And for the third time in four years, a place in the final at the grass-court major will be on the line. This time, a dominant World No. 1 in Sinner chasing his first Slam final of the season will try to halt Djokovic’s pursuit of his 25th major trophy aged 39.
“Of course, in a sense, it is really a nice surprise. But at the same time, I always have the highest expectations for myself,” Djokovic said after his fourth-round victory against Auger-Aliassime. “I can be very self-critical, very hard on myself. At the same time, I try to also enjoy the moments like this.
“I don't know what tomorrow brings. To be honest, let's see. I'm still in the tournament. I still want to go at least one more step further. But this was as good as a final for me.”
But anyone who has followed Djokovic’s career knows that his pursuit of history is insatiable. It is with that hunger and determination that the man who has held No. 1 in the PIF ATP Rankings for an astonishing 428 weeks in his career has rewritten the sport’s record books. And after a memorable performance against the third-seeded Canadian, he will try to take advantage of his two days’ rest to prepare for the challenge ahead.
On one hand, the 101-time tour-level titlist knows that recovering and taking down Sinner will be a big ask. But on the other, the Serbian did just that at this year’s Australian Open, ousting the two-time defending champion in five sets.
“I had a very long semis against Sinner. This is quarters. Now I have to play Sinner in semis. There's difference and difference in the surface. Obviously that was the first big tournament of the year for me, coming fresher from several months of break and preparation,” Djokovic said. “It's a bit different now. But nevertheless, another great, historic run for me at the Grand Slams. This is what counts the most, honestly.
“I still try to prove to myself and others that I'm able to compete with the best players in the world and beat them in the biggest stage. That's what I've done in Australia. It's what I've done here.”
It is a critical match for Sinner, too. It has been a historic season for the 24-year-old, who has swept all five ATP Masters 1000 events of 2026. In Madrid, he became the first player to claim five consecutive Masters 1000 titles, and in Rome he earned his sixth in a row.
But the Wimbledon top seed has not made a major final this year after a stretch of advancing to the championship match at five straight Grand Slam tournaments. The San Candido native will also have Djokovic’s triumph against him from Australia in back of mind.
Sinner takes a 6-5 Lexus ATP Head2Head lead into Friday’s showdown, but Djokovic has won two of their three Wimbledon meetings. However, Sinner has won five of their past six matches and will try to take advantage of being fresher, having not lost a set since the first round.
“I feel like every match is different. Even when I had this small streak with him, I felt like every match has really its own story. Especially when you play on a surface like this, if you have a bad serving day or not feeling the ball very well, it's going to be very, very tough,” Sinner said. “In any case, I'm happy to be back in the semis. I'm happy to fight for every ball, then we’ll see.”
The serve will prove critical. As Djokovic showed in his final-set tie-break against Auger-Aliassime, he still has the ability to go into “lockdown mode” from the baseline. The big question will be whether Sinner will allow him to settle into such a rhythm. The top seed knows the difficulty of the challenge in front of him.
“He has won this tournament so many times and he knows exactly how to approach it,” Sinner said. “I’m looking forward to it.”