Five little wolves

Fernando Murciego | 31 Mar 2025 | 17.11

Jakub Mensik, the last U20 capable of toppling Novak Djokovic. Source: Getty

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The younger ones will come and the older ones will leave. I don't know if the saying is exactly like that, I'm not even sure if it's a saying. What I do know is that the passage of time is inherent to the constant renewal of sectors, even the human one. Novak Djokovic is one of those trying to escape this regeneration, although it is evident that each day it will be more difficult for him to block the path for the younger ones. In his twenty-year career, only five players under the age of 20 have managed to defeat him in an ATP tournament, with Jakub Mensik being the latest to join this group. I think today is a good time to review who these young wolves were who found the formula to tame the big wolf.

FILIP KRAJINOVIC

And we start with one of those almost impossible-to-believe stories. Filip Krajinovic was just 18 years and 2 months old, a tender player who in May 2010 had yet to experience winning an ATP match. With that excitement, he showed up at the ATP 250 in Belgrade thanks to a wildcard, unable to access the main draw otherwise being outside the top 300. Suddenly, two victories (over Donskoy, Zeballos) placed him in the quarterfinals, where he faced the world No. 2, also an absolute idol of the country: Novak Djokovic. That triumph will forever remain in everyone's memory, although the negative note was the outcome, with Djokovic forced to retire due to injury after losing the first set 6-4. For the records, Krajinovic remains to this day the youngest player in history (up to that moment) capable of defeating Djokovic.

STEFANOS TSITSIPAS

Facing a player for the first time always carries some danger, regardless of their level or age. What happened at the 2018 Canada Masters 1000 is a good example, with Djokovic overshadowed in the round of 16 by a 19-year-old and 11-month-old youngster who was already in the top 30. It was the season of Stefanos Tstsipas' breakthrough, the year of breaking into the top of the rankings, a milestone he achieved with victories like that one that day (6-3, 6-7, 6-3). In fact, the Greek can boast of having beaten the Serbian in two of their first three encounters. After that, things turned around as he lost the next eleven matches. The Greek player never would have imagined aging so poorly in their head-to-head encounters.

CARLOS ALCARAZ

At 19 years and 2 days old, El Palmar's genius didn't need more time to enchant the entire audience at the Caja Mágica by playing the best three-set ATP match of 2022. The Spanish player came in strong, having just won the title in Barcelona the previous week and was on a roll at the Mutua Madrid Open. He didn't hesitate in the quarterfinals to push aside his idol, Rafa Nadal, but the real feat came a day later against the Serbian (6-7, 7-5, 7-6). Just like with Krajinovic or Tsitsipas, that was also their first meeting, emphasizing once again that surprise factor that often works against the locker room's titans. Doing it at these ages is twice as commendable.

HOLGER RUNE

And six months later, though six months older, a Danish lad with the look of a troublemaker appeared, along with that necessary audacity to make a statement. From the same generation as Alcaraz, although always two steps behind in terms of progression. At Paris-Bercy 2022, Holger Rune wanted to make a breakthrough and for that, he had no choice but to break a barrier that had never been seen before: a player under 20 snatching a title from Novak Djokovic. As if the plan didn't already carry extreme difficulty, that 19-year-old and 6-month-old lad worked a miracle by coming back after losing the initial set (3-6, 6-3, 7-5), overturning all predictions and thus capturing the biggest title of his career. It must be said, he's still dealing with the aftermath.

JAKUB MENSIK

The latest addition to this list of young wolves belongs to the generation that grew up watching Novak's matches on TV. "You are one of the main reasons I became a professional tennis player," Jakub Mensik said to him during last night's trophy ceremony at the Miami Open 2025. While his entire tournament had been brilliant, there is an immense gap between beating Djokovic in a Masters 1000 final and anything else, but it's been a while since the men's locker room has seen the impossible happen. In a hard-fought match with two tiebreaks (7-6, 7-6), the Czech reached the sky in Florida to break a few records of precocity (19 years and 210 days,), also making a global name for himself through that match that he'll never forget. Who will be the next to join this list of talents? If it were up to Djokovic, it might as well end here.

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