Novak Djokovic is still chasing that elusive 100th title. Only five players in the Open Era have cracked the century mark, with Roger Federer being the most recent. But since standing atop the Olympic podium last July, Djokovic has had an uncharacteristic dry spell. The 37-year-old tennis champion finally found himself in a title match in Miami—first since Shanghai Masters last year. But the wait for number 100 continues after a gut-wrenching loss to a 19-year-old. Even an American icon is commenting on his lost opportunity.

The 24-time Grand Slam champion’s 2024 season saw him make two final appearances—at Wimbledon and Shanghai Masters—losing to youngsters Carlos Alcaraz and Jannik Sinner, respectively. Entering 2025, he struggled to get back on track. His best chance came at the Australian Open, his happy hunting ground. Djokovic looked poised to strike, reaching the semi-finals before a muscle tear forced him to withdraw mid-match. From there, it was a series of surprising early exits for the Serbian legend.

The Miami Open saw Djokovic make a stunning run. He bulldozed through the draw without dropping a set, becoming the oldest finalist in a Masters 1000 event. At 37, he stood on the opposite side of the net from one of the youngest players in the field, 19-year-old Jakub Mensik. Having won the Miami title a record six times, Djokovic was the clear favorite, but in a shocking turn of events, the Czech teenager pulled off a 7-6, 7-6 stunner, denying the Serbian his century.

The former player and commentator, Patrick McEnroe, took to X, writing, “Wow. Mensik unreal. He wins @MiamiOpen over @DjokerNole 7-6 7-6 Title 100 will have to wait.” This is in stark contrast to McEnroe’s earlier bold prediction regarding Novak Djoković’s Miami Open outcome.

On March 30th, Novak Djokovic’s dominant march to the Miami Open final saw him win all five of his matches without dropping a set. In the semi-finals, he faced Grigor Dimitrov, who struggled considerably, racking up 32 unforced errors in the match. Subsequently, Patrick noted, “Today @DjokerNole will win his 100th career title @MiamiOpen. He will join 2 other male players in the 3-digit category. Who are they? Do not google it.” The answer: Jimmy Connors (109 titles) and Roger Federer (103 titles).

Novak Djokovic’s 99 Titles by Region:

• Europe: 44
• North America: 22
• Australia: 12
• Asia: 13
• Middle East: 8
• South America: 0

The buzz around the match was intense, made even crazier by a nearly six-hour rain delay in Florida. When play finally began, Mensik wasted no time making his mark. He broke Djokovic at the first opportunity and stormed ahead 4-1. His first serve was on fire, while Djokovic struggled to find his rhythm. The Serbian even had to pause to apply eye drops for swelling under his right eye and used sawdust to manage his grip in the humid conditions.

The 37-year-old eventually settled in. His serve sharpened, and his signature backhand slice began to trouble Mensik. The teenager’s nerves showed as he handed back the break, and soon enough, a tie-break was looming. Djokovic, though, stumbled at the start of it. He saved two set points, but Mensik held firm and blasted his way to the opener.

This match felt eerily similar to their clash in Shanghai last year, where Mensik took the first set in a breaker before fading. But this time, the Czech refused to back down. He kept up his intensity, and despite the Serbian’s best efforts, the Czech starlet sealed the match in straight sets.

Fun fact: In July 2006, Novak Djokovic captured his maiden ATP title at the Dutch Open in Amersfoort, a now-defunct clay-court tournament. This victory propelled him to a career-high ranking of No. 36 at the time.

Despite the disappointment, Djokovic showed nothing but class in defeat.

Novak Djokovic admits Jakub Mensik was “better” than him

Novak Djokovic’s known about Mensik’s potential for years and even played a role in his journey. Back in 2022, Djokovic saw Mensik lose a tough three-setter in the Australian Open boys’ final and was impressed. He reached out through his management team, setting up training sessions for Mensik at his club in Belgrade. It was a kind gesture to someone who considers Djokovic his “tennis inspiration” 

“Congratulations to Mensik and his team. Never really happy to lose, but he’s one of the very few players that I would be happier to lose to, to be honest,” Djokovic said. “I have seen him play when he was 15 or 16 and invited him, we had some training blocks together. He was training at my club in Belgrade, and to see his development and evolution is really great, amazing.”

The 6-time Miami Open champion gave full credit to the Czech teenager’s performance. He said, “It hurts me to admit it, but you were better! In the clutch moments, you delivered the goods [with] unbelievable serving and just a phenomenal effort mentally as well to stay tough in a difficult moment.”

There is good news for Djokovic, though. After a shaky start to 2025, he is finding his form. His run in Miami has set him up to fourth in the PIF ATP Live Race To Turin. Up next? The Monte Carlo Masters that begin next week. Djokovic hasn’t won there since 2015, but he came close last year, reaching the semi-finals. Will Monte Carlo finally be the place where Novak Djokovic joins the century club?