With a record 24 Grand Slam titles to his name, it's hard to argue with the opinion of Novak Djokovic being the greatest tennis player of all time. Sure, some will point to fellow greats Roger Federer and Rafael Nadal, but while those two were winning slams against the likes of Mark Philippoussis and Mariano Puerta, Nole was regularly beating both resident 'Big Four' members, as well as Andy Murray.

However, at the ripe old age of 38, the Serbian now stands in unfamiliar territory, with the waiting game for Grand Slam number 25 having become one of the court's most fascinating subplots. Many top news outlets thought his ongoing drought could come to an end at Wimbledon back in August. The popular Bodog News Canada site mentioned the Djokovic prominently in their pre-tournament write-up for the showdown at the All-England Club showdown, touching on him as a 13/2 shot to watch. However, his quest for a record-equalling eighth crown was ended in the semifinals by eventual champion Jannik Sinner.

With the emergence of both the aforementioned Sinner and Patrick Mahomes, there's a very real chance that Djokovic's ongoing drought will only end with the Serbian's retirement. But what of his previous career droughts? How long did they last? And how did they eventually come to an end? Let's take a look.

Flip back to that electric night in the Big Apple, September 2023. Djokovic, emotionally spent and victorious, collects Slam #24—tying Court, pulling clear of Federer and Nadal, and sharing a tearful embrace with his daughter courtside. Three major trophies in a calendar year had the tennis world wondering if two dozen would quickly become 25. But sport, as always, delights in rewriting the script.

Since that moment, Grand Slam silverware has proven elusive. Eight majors and counting—each tournament unfurling a new storyline, but always culminating with Djokovic on the outside looking in. The ghosts of youth have new names and new swagger: Carlos Alcaraz carving up Wimbledon grass and Big Apple hardcourts; Jannik Sinner, ice-veined and resilient, denying Djokovic in Paris and again on Centre Court.

Still, if anyone expects him to bow out quietly, they haven’t watched Novak Djokovic stalk the baseline. At the 2025 US Open, in a defiant throwback performance against Taylor Fritz, Djokovic did what champions do best: he fought, adapted, and refused that easy exit.

If the present drought feels surreal, it’s not entirely uncharted territory. Djokovic’s post-2016 French Open drop-off remains one of the sport’s great cautionary tales. That Paris title was meant to confirm his invincibility—all four Slams held simultaneously, a feat not seen since Rod Laver. The career grand slam was secured at long last, and surely a decade of domination was to come. Well, not so fast.

First came the shocker: Wimbledon 2016, and the unheralded Sam Querrey snapping Djokovic’s 30-match Slam win streak. At Flushing Meadows, he would go on to reach the final, only to be stunned by a Swiss sensation. Nope, not Federer, but Stan Wawrinka, announcing his own emergence as a major player.

By 2017, Nole's elbow was in revolt. He wouldn't make it past the quarterfinals at any of the four slams, with his injury then forcing him to abandon the US Open and finish the season outside the top 20 for the first time in more than a decade. The first half of 2018 brought similar woes, a fourth-round Aussie Open stunner at the hands of unseeded Korean Chung Hyeon, before a shock quarterfinal loss to Italy's Marco Cecchinato at the French Open.

Yet, somewhere in the wreckage, Djokovic rediscovered his brilliance. He tore down old routines and, under the steady gaze of coach Marian Vajda, built them anew. The 2018 Wimbledon run was a hard reset, rediscovering his swagger in a five-set semi-final thriller against old rival Nadal, before dispatching underdog Kevin Anderson in straight sets in the final. A two-plus-year drought banished, and a torrent of emotion rarely glimpsed from the normally inscrutable Serb was finally released.

For all his late-career reinventions, it’s easy to forget that Djokovic’s early trajectory was far from linear. After a stunning Australian Open triumph aged just 20 in 2008, the narrative seemed set: a new Big Three had emerged. But 11 consecutive majors would come and go before Grand Slam title number two.

Despite Nole claiming his maiden crown, the tennis world was still dominated by two men: Federer and Nadal. They carved up ten of the next 11 Slams following what appeared to be Djokovic's coming-out party. However, in 2010, five master's titles suggested that the young prodigy was finally ready to take on tennis's undisputed kings.

Then, 2011 happened: a bulldozing Australian Open final, a 41-match win streak, and three Slams in a single year. This drought didn’t just build a player; it birthed a force of nature that would ultimately morph into the GOAT we know and love today.

Even at his peak, Djokovic has known the sting of lost opportunity. Between his thunderous Australian Open win in 2012 and Wimbledon magic in 2014, he became, for once, the nearly man: three major finals reached, three lost. If the numbers were still gaudy, the experience underscored how hard mere consistency can be at the sport’s summit.

Cue a bold move—hiring Boris Becker, the legend with the gameday steel that Djokovic sought. The duo set out to crack the code of close contests: how to win ugly, how to stay present under withering pressure. The dividend came in the summer of 2014. In yet another Wimbledon epic, Djokovic outdueled Federer in five enthralling sets. Suddenly, the drought and the self-doubt that accompanied it dissolved into another historic run.