Teenage players who beat Novak Djokovic on ATP Tour

Only five teenage players have defeated Novak Djokovic on the ATP Tour.

Novak Djokovic looked set to win his first title on Tour in over a year, but unseeded Jakub Mensik came his way. Beating the Serbian tennis star is always a tough task for any player, and only a handful of players have a winning record against him.

The Serb is admired for his longevity and fitness, even at the age of 37. Despite a knee injury, he won his long-awaited men’s singles gold at the 2024 Paris Olympics. In addition to a strong in-game dynamic, Djokovic is also a mental wizard.

Given his overall ability, he becomes difficult to defeat and often requires a lot of experience. However, at a few junctures, teenagers have handed the 24-time Grand Slam champion a shocking defeat. On that note, here we take a look at the teenage players who beat Novak Djokovic on the ATP Tour.

Filip Krajinovic: 18 years, 2 months, and 10 days

The first teenager to win against Djokovic was his countryman Filip Krajinovic. The 24-time Grand Slam champion was seeded first at the 2010 Belgrade Open. He began his campaign with a win over Italy’s Fabio Fognini but was forced to withdraw from the third round due to fitness concerns.

The Serb had breathing issues. In his next match, he faced 18-year-old Filip Krajinovic, who was entered into the main draw as a wildcard. Krajinovic later reached the semifinals in Belgrade, where he lost to eventual champion Sam Querrey.

Carlos Alcaraz: 19 years, 2 days

The most anticipated name on the list, Carlos Alcaraz, has given Djokovic neck-to-neck competition in all their matches. The two faced each other for the first time in the semifinals of the 2022 Madrid Open. At the same tournament, he became the first player to record at least 30 singles wins at all nine Masters 1000 events.

However, his run was halted in the semifinals when he clashed with Carlos Alcaraz. Seventh seed Alcaraz defeated his idol, Rafael Nadal, in the quarterfinals and later played a three-setter against the Serbian in the last four. After losing the first set on a tiebreak, the four-time Grand Slam champion claimed the victory 7-6 (7-5), 5-7, 6-7 (5-7).

Holger Rune: 19 years, 6 months, 8 days

After losing to Carlos Alcaraz in the Madrid Open, Djokovic’s party in Paris was spoiled by another emerging star, Holger Rune. The Dane announced himself to the tennis world at the 2022 Paris Masters. He started his campaign by beating Stan Wawrinka in the first round.

In the second round, Rune defeated the 10th seed Hubert Hurkacz in straight sets. He then stunned Andrey Rublev in the third round. Rune faced his friend Carlos Alcaraz in the quarterfinals, but the Spaniard had to retire due to an injury.

After defeating Canada’s Félix Auger-Aliassime in the semifinals, Rune was set to lock horns against Novak Djokovic in the final.

Nevertheless, 19-year-old Holger Rune stunned the 24-time Grand Slam champion 3-6, 6-3, 7-5 to win the prestigious Masters title.

Jakub Mensik: 19 years, 6 months, 29 days

Czech tennis star Jakub Mensik became the first teenager to beat Novak Djokovic in straight sets in the 2025 Miami Open final. The final was delayed for almost six hours, and when the match started, the 19-year-old outplayed the Serbian wizard with his impeccable second-serve accuracy and ace-smashing efficiency.

Both sets were forced into a tiebreak, but the Czech international stood strong and pulled off a 7-6 (4), 7-6 (4) victory. The 19-year-old was not seeded at the Miami Open, and still holds a winning record against top 10 players (8-5) and even top 5 players (3-1).

Interestingly, Mensik grew up idolising the 24-time Grand Slam champion and worked hard enough to make him his on-court rival.

Stefanos Tsitsipas: 19 years, 11 months, 28 days

Two-time Grand Slam finalist Stefanos Tsitsipas beat Novak Djokovic for the first time on Tour when he was a teenager. At the 2018 Canadian Open, the Greek tennis star enjoyed a stellar campaign with a bitter end. He beat former US Open champion Dominic Thiem in the second round.

However, one of his biggest wins came in the third round, where he faced Djokovic. In a tough match, Tsitsipas won the first set but lost the second set in a tiebreaker. The game was forced into a decider, where the two-time Grand Slam finalist succeeded.

It was also the first meeting on the tour between Tsitsipas and Djokovic. However, the Greek tennis star has failed to win a match against the 24-time Grand Slam champion since 2019, as he leads the tally 12-2.

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