There’s little doubt that Novak Djokovic is inching closer to a historic 100th ATP singles title — a milestone that now feels more like a matter of “when” rather than “if.” But while the century mark seems within arm’s reach, seasoned tennis broadcaster Gigi Salmon has voiced her skepticism about the Serb’s prospects of claiming that elusive 25th Grand Slam crown.
The Serbian maestro, who etched his name further into tennis history with Olympic gold at the 2024 Paris Games — defeating Carlos Alcaraz in a career-defining final to complete the rare Career Golden Slam — has been sitting on 99 career titles since that golden summer moment. Since then, however, the road to title No. 100 has been trickier than many anticipated.
In the seven tournaments he’s entered post-Olympics, Djokovic has been consistently close but just short of the finish line. He posted runner-up finishes at the Shanghai Masters last October and most recently at the 2025 Miami Open, where he was outclassed by rising Czech sensation Jakub Mensik in a straight-sets defeat during the final.
Not the Same Walk in the Park
At 37, Djokovic is battling not just his opponents, but also time — a reality Salmon noted in her Sky Sports Tennis column.
“Things tend to get harder with age: recovery from strenuous exercise, a big night out and in some cases achieving our goals and dreams, something 37-year-old Novak Djokovic is finding as his quest for title 100 continues,” she wrote.
Reaching his eighth Miami final — and the 142nd of his astonishing career — Djokovic hadn’t dropped a set leading up to the showdown with Mensik. His court movement was sharp, his serve precise, and his footwork as fluid as ever. But on Sunday, he met a fearless 19-year-old who idolized him growing up — and who hadn’t even been born when Djokovic played his first Masters 1000 event. Mensik, making his Masters final debut, seized the moment and stunned the legend.
Grand Slam No. 25: A Dream Deferred?
If Djokovic’s chase for his 100th tour-level title feels like a slow burn, his hunt for a 25th Grand Slam has hit an even more frustrating pause. Since lifting the US Open trophy in 2023 — his record-breaking 24th major — Djokovic has yet to add another Slam to his glittering collection.
His best shot came at Wimbledon last year, where he reached the final but was outplayed by Alcaraz in straight sets. And in 2025, his Grand Slam campaign started on an unexpected note — forced to retire in the Australian Open semi-final due to a hamstring issue during his clash with Alexander Zverev.
Salmon reflected on the increasing difficulty of such monumental feats, especially at this stage in Djokovic’s career.
“When it comes to Djokovic, the articles celebrating a new record and new piece of history are written and ready to go,” she wrote. “And while I’m not certain the 25th Grand Slam will be won, I’m sure the 100th title will be secured, with his next opportunity the Masters 1000 in Monte Carlo, a title he has won twice before but not since 2015.
“He seems to have renewed motivation, but the task doesn’t get any easier and one thing is clear: he will need to keep playing matches in order to have the sharpness and confidence to try for 25.”
A Packed Clay-Court Path to Paris
With Roland Garros looming in May, Djokovic is poised for a busy stretch on the red dirt. Before he targets the Coupe des Mousquetaires once again, he’ll look to build momentum through a trio of pivotal tournaments.
First up: Monte Carlo, a venue that has eluded his grasp for nearly a decade. Following that, he’ll head to the Spanish capital for the Madrid Open, and then wrap up his pre-Roland Garros preparation in Rome at the Italian Open — a city where he’s hoisted the trophy multiple times.
The Final Stretch?
Whether Djokovic adds to his Grand Slam haul or not, his pursuit of title No. 100 promises to be another defining chapter in an already legendary career. The milestones may be getting harder to reach, but the fire clearly still burns.
And as new stars like Mensik and Alcaraz continue to rise, Djokovic finds himself in a fascinating position: both the standard and the target, still capable of brilliance — but facing a new generation eager to write their own legacy.