The Shanghai Masters has taken quite the turn this year. With top seeds Carlos Alcaraz and Jannik Sinner, among others, off the court due to illness and injury, the path is wide open for the final 16. Novak Djokovic is cruising through the Masters 1000—well, almost. He booked his round of 16 spot after edging out German qualifier Yannick Hanfmann 4-6, 7-5, 6-3. But in the humid Shanghai conditions, even Nole hit a wall. He threw up mid-match before pushing through to victory. Now, he’s facing Jaume Munar. But is it feeling a bit better?

The Serb started Tuesday’s match against the Spaniard looking sharp, breaking early for a 3-1 lead in the first set. Then the momentum shifted. Right after the changeover, he called for a medical timeout. Fans on X caught it instantly, one post reading, “MTO for Novak’s ankle, right after the break. It hurts. ❤️🙏.”

Djokovic grimaced and clutched his Achilles as the trainer checked on him at 3-1. His hamstring was already strapped, but he pointed directly to the back of his ankle while receiving treatment. After a quick on-court massage, he continued and held serve for 4-1. Yet the pain was written all over his face.

At the next changeover, he called the physio again, biting down on his towel in frustration. Commentator Ryan Harrison observed, “He’s definitely pointing at the Achilles behind,” as replays showed the exact moment Djokovic winced after a hard movement. Through it all, the 24-time Grand Slam champion kept fighting, refusing to hand over the court easily.

And if you thought the fight was over, then it was far from it. Novak Djokovic battled through a wild second set, vomiting courtside multiple times and collapsing to the floor after dropping it, before getting medical help. Yet, in brutal conditions, the 38-year-old dug deep to wear down Munar 6-3, 5-7, 6-2 in one of the season’s most grueling clashes.

While Nole picked up the pace in the second set, he was unable to withstand the extreme temperatures. Giving a flashback to his match against Yannick Hanfmann, when he threw up on the court!  After that match he pointed out how tough the challenge was, “It’s brutal when you have over 80 per cent of humidity day after day, particularly for the guys when they’re playing during the day with heat, with sun, it’s even more brutal. For me, biologically it’s a bit more challenging to deal with it. But I had to really weather the storm today.”

And yet, it repeated itself today including an ankle injury scare. Although, physical woes have been an ongoing issue for Novak Djokovic this season.

Novak Djokovic’s struggle with injury and illness continues

Back in January, Novak Djokovic kicked off the 2025 season with big hopes—chasing his 100th ATP tour title, which he conquered at the Geneva Open, and eyeing a historic 25th Grand Slam. He made it to the semifinals in all four majors this year but hit roadblocks against top players like Jannik Sinner and Carlos Alcaraz. His first major setback came at the Australian Open when injury struck during a tough quarterfinal against Alcaraz. Despite the pain, Djokovic pushed on to the semis to face Alexander Zverev.

In the semifinal match, Djokovic’s fight was real but short-lived. After losing the first set 7-6(5), he revealed he was battling a muscle tear. “I did everything I possibly can to basically manage the muscle tear that I had,” he said. The pain intensified fast, making it impossible for him to continue. Eventually, Nole had to withdraw, handing the match to Zverev and raising serious questions about his physical future.

Reflecting on his career and current struggles in a post-match interview, Novak Djokovic was candid: “This is probably the new reality I have to accept—that my body will probably betray me more often than it has throughout my entire career.” Memories of last year’s French Open injury also loomed, where Novak withdrew due to a torn medial meniscus in his right knee. Uncertainty clouds what’s next, but he remains cautiously optimistic: “How much I’ll be able to put up with that and endure that, I honestly don’t know now. Let’s see what happens this season.” But the challenges didn’t stop there.

He was initially expected to stay off the court until June, around Roland Garros, but returned earlier for the Qatar Open in February. The comeback didn’t go as planned, ending in a first-round defeat — a result that repeated at Indian Wells. March brought another setback at the Miami Open, where Djokovic battled a swollen, infected eye that worsened as the tournament progressed. Eye drops offered little relief, and the discomfort affected his vision and performance, cutting into his preparations for the Monte-Carlo Masters.

Then came a string of physical blows: a lower back injury at the US Open, neck and forearm trouble, thigh and hamstring strains, and a nasty slip at Wimbledon, all testing the Serbian’s resilience yet again.

Now, as Djokovic heads into the Shanghai Masters quarterfinals for the 11th time, all eyes are on whether he can overcome these persistent issues. His last ATP Masters 1000 title came at the 2023 Paris Masters. But now, will Shanghai, his favorite event, be the stage for a comeback? We’d love to hear what you think in the comments below!