Jack Draper beat Novak Djokovic in the round of 16 at Indian Wells on March 12 and became the only fifth player to defeat the legendary Serbian in the last 12 months. The match went the distance in every sense with a 4-6, 6-4, 7-6(5) victory for the top-ranked Brit.

Draper produced a performance worthy of a defending champion in the first ATP 1000 event of the season. Novak Djokovic was chasing his first Indian Wells title since 2016 and for one set it looked like he might get there. Then Draper found his momentum and did not let go.

For most of his career, Novak Djokovic shared the burden of being the best with Roger Federer and Rafael Nadal. The three of them pushed each other to levels the sport had never seen and the losses, when they came, were mostly confined to that group. Federer retired in 2022 and Nadal walked away in 2024, and the arena changed completely.

Carlos Alcaraz and Jannik Sinner stepped into the conversation and became Novak Djokovic's primary obstacles in this new era. Those two get most of the attention when his losses are discussed, and that makes sense because they are arguably the best players in the world right now. But they are not the only ones who have beaten him over the past twelve months.

Only five players outside the current top two have gotten the job done against the 24-time Grand Slam champion in the last 12 months, and each of those results tells its own story.

Players who beat Novak Djokovic in the last year that were not Alcaraz or Sinner

1. Jack Draper - Indian Wells, March 2026

Jack Draper defeated Novak by 4-6, 6-4, 7-6(5)
Jack Draper defeated Novak Djokovic for the first time (Image Source: X/SkySports)

Jack Draper missed a chunk of late 2025 through injury and came into Indian Wells needing a strong run to prove his 2025 title was not a one-off. He got it in the best possible way. Novak Djokovic took the first set 6-4 and looked comfortable. Draper came back in the second, started using his heavy left-handed forehand to push Djokovic deeper and deeper behind the baseline, and won it 6-4.

The third set was tight throughout. A long rally early in the set took a lot out of Novak Djokovic physically, and by the time the tiebreak arrived, Jack Draper had more left in the tank. He closed it out 7-5. Djokovic said afterward that losing a match that close felt bitter. Draper was just the fresher and better player on the day.

"[I have] a bitter feeling right now, losing a match like this," Novak Djokovic said in his post-match press conference. "But proud of myself for fighting and really giving it all on the court. That's for sure. That's the one thing that I'll take as a highlight. Just the fact of not giving up and trying. I lost to a great player, and it was really such an even match throughout the entire two-and-a-half hours. But I am just a bit disappointed."

2. Valentin Vacherot - Shanghai Masters, October 2025

Valentin Vacherot won by 6-3, 6-4
Vacherot defeated Novak Djokovic in the Shanghai semi-finals (Image Source: X/TheTennisLetter)

Valentin Vacherot was ranked No. 204 in the world when he played Novak Djokovic in the Shanghai semi-finals. He was a qualifier who had no business being anywhere near that stage of the draw. Djokovic was struggling physically throughout the week, had been dealing with cramps and heat stress, and had reportedly been sick courtside in earlier rounds.

His movement was restricted, and Vacherot, playing with nothing to lose, hit through him from the baseline and threw in well-timed drop shots whenever Novak Djokovic tried to hold his ground. He won 6-3, 6-4 in 31-degree heat. It was one of the most unlikely results in Masters tennis in years, and it cost Djokovic what would have been a record 41st Masters title.

3. Matteo Arnaldi - Madrid Masters, April 2025

Matteo Arnaldi beat Novak Djokovic in the first round of Madrid 6-3, 6-4 and it was not particularly close. Djokovic was coming into the clay season looking for form and found none of it in this match. He made 32 unforced errors, 20 of them in the first set, and never got comfortable on serve or return.

Arnaldi grew up watching Djokovic win everything and played with no fear at all. He was aggressive from the first point, saved four of five break points he faced and gave Djokovic no rhythm to work with. After the match Djokovic said he might have just played his last match in Madrid. It was that kind of afternoon.

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4. Alejandro Tabilo - Monte Carlo, April 2025

Alejandro Tabilo beat Novak Djokovic in Monte Carlo 6-3, 6-4 a few weeks before the Madrid loss and made it 2-0 in their head-to-head record. He is a left-hander from Chile whose heavy topspin forehand kicks up high out of Djokovic's comfortable hitting zone on clay and Djokovic has not found a consistent answer to it across two matches now.

Djokovic made 29 unforced errors, looked a step slow all match, and described his own performance as horrible. It was his clay court opener for 2025 and it set the tone for a difficult few weeks on dirt. Two straight-sets losses to players outside the top 40 in Monte Carlo and Madrid back-to-back was not something anyone had predicted heading into that part of the season.

5. Jakub Mensik - Miami Masters Final, March 2025

Jakub Mensik was 19 years old and playing in his first ATP final when he beat Novak Djokovic 7-6(4), 7-6(4) in Miami. Djokovic was going for his 100th career title. Both sets went to tiebreaks and Mensik won both. He served 14 aces and played with a confidence that most teenagers do not have in their first final, let alone their first final against a 24-time Grand Slam champion.

Djokovic had an eye infection going into the match and slipped on court at one point but still took both sets to tiebreaks. Mensik was just better in the moments that decided it. He became the lowest-ranked Miami champion in the tournament's history, and in doing so, he sent a message that the next generation is no longer walking onto court against Djokovic with any sense of being outranked or outclassed. That shift matters more than any single result.