Is Novak Djokovic in a time loop? Because no matter the year, the tournament, or the opponent, he just keeps making history. And once again, he has found himself in familiar territory— competing with Roger Federer. Even with the Swiss legend retired, their rivalry lives on in the record books. On Friday, the Serbian defeated Grigor Dimitrov 6-2, 6-3 in the Miami Open semifinals, securing yet another milestone. At 37 years and 10 months old, he became the oldest player to reach a Masters 1000 final, surpassing Federer’s 2019 record of 37 years and 7 months. And here’s the kicker—they both hit this achievement at the Miami Open. Talk about a coincidence! But the Djokovic-Federer parallels don’t end there.
Their rivalry, one of the greatest in tennis, dates back to 2006. Federer dominated early on, but Djokovic turned the tide with his first victory in 2007. They clashed 50 times, producing legendary battles across all surfaces. The head-to-head? Djokovic leads 27-23. And then there’s the Sunshine Double. Both Federer and Djokovic have thrived in Indian Wells and Miami, becoming the only players to win both tournaments three times in a row. Federer conquered it in 2005, 2006, and 2017, while Djokovic went on a tear in 2011, 2014, 2015, and 2016. If that wasn’t enough déjà vu, Djokovic matched another Federer milestone after his semifinal win. By reaching the final, the 37-year-old extended his streak to 20 consecutive seasons of competing in a tour-level final—tying Federer’s all-time record. Some things in life are inevitable: death, taxes, and Djokovic and Federer rewriting history.
Now, the Serbian is closing in on another major feat—his 100th career title. His chase began with his Paris Olympics win in July 2024, and he could finally hit the century mark in Miami. Federer, of course, got there first, winning his 100th title at 37 against a young Stefanos Tsitsipas. And as tennis insider Bastien Fachan pointed out in a post on X, history might just repeat itself. He noted, “Roger Federer won his 100th title at 37 against Stefanos Tsitsipas, born 1998, his first year on tour, who grew up idolizing him. Novak Djokovic could win his 100th title at 37 against Jakub Mensik, born 2005, his first year on tour, who grew up idolizing him. Cinematic parallels.”
Roger Federer won his 100th title at 37 against Stefanos Tsitsipas, born 1998, his first year on tour, who grew up idolizing him
Novak Djokovic could win his 100th title at 37 against Jakub Mensik, born 2005, his first year on tour, who grew up idolizing him
Cinematic parallels
— Bastien Fachan (@BastienFachan) March 29, 2025
Jakub Mensik, the 19-year-old Czech, pulled off a stunner on Friday, defeating world No. 4 Taylor Fritz 7-6(4), 4-6, 7-6(4) to reach his first Masters 1000 final. And just like Tsitsipas idolized Federer, Mensik has looked up to Djokovic since childhood.
“My tennis inspiration is Novak Djokovic. Because of him, I started to play tennis. He is my biggest idol. And because of him, I wouldn’t be here,” the Czech tennis starlet told the ATP Tour last year.
Mensik has more than admiration for Djokovic—he’s had a helping hand from him, too.
Jakub Mensik reveals how Novak Djokovic helped him
In 2022, Novak Djokovic surprised the young Czech with a phone call, offering advice and support. Mensik, shocked at first, realized it was the real deal.
“He did not hesitate to share his knowledge and contacts. We had closed doors in front of us, Novak opened them,” Mensik told *L’Equipe* in 2024. That call led to a training session in Belgrade, where Mensik observed Djokovic up close. He mimicked every detail, soaking up knowledge from the 24-time Grand Slam champion. “Weight, lunch, recovery… Everything he did, I did. I understood a lot of things there. I observed him, I tried to analyze his functioning, how he warms up, stretches, recovers,” the 19-year-old explained.
Now, the student faces the master with a chance to make history. Djokovic is eyeing his 100th singles title, his seventh Miami Open crown, and a record-extending 41st Masters 1000 title. Meanwhile, Mensik, ranked 54th before the tournament, has jumped 24 places to 30th in the Live ATP Rankings. Only five teenagers in the past 20 years have reached a Miami Open final—Rafael Nadal (2005), Djokovic (2007), Jannik Sinner (2021), Carlos Alcaraz (2022), and now Mensik.
The last time Djokovic and Mensik met, it was a three-set battle in the Shanghai Masters quarterfinals. Now, with the stakes higher than ever, the question remains: Can Mensik pull off the ultimate upset, or will Djokovic once again cement his place in history? Who’s your pick for the Miami Open title? The protege or his idol?
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