When Did Novak Djokovic Last Lose In A Grand Slam First Round?

Novak Djokovic's first-round defeat to Mariano Navone at the 2026 US Open ended a remarkable two-decade run. The 39-year-old had not lost his opening match at a Grand Slam since the 2006 Australian Open.

Djokovic's 7-6(5), 5-7, 4-6, 6-2, 6-1 defeat to Navone in New York lasted four hours and 36 minutes, making it the longest opening-round match of his Grand Slam career. It also snapped his 78-match winning streak in the first round of majors - the longest such streak by a male player in the Open Era.

Novak Djokovic's Last First-Round Grand Slam Defeat

The last time Djokovic exited a Grand Slam in the opening round was at the 2006 Australian Open, 20 years before his loss to Navone.

Djokovic was then an unseeded qualifier ranked outside the world's top 100. Having fought through qualifying to reach the main draw in Melbourne, the Serbian faced American Paul Goldstein, who was ranked No. 68 in the world.

Goldstein defeated the then-18-year-old Djokovic 6-2, 1-6, 6-3, 6-2.

At the time, it was difficult to imagine what Djokovic's career would become. The Melbourne defeat remained his only first-round loss at a Grand Slam for the next two decades.

What Happened Between 2006 And 2026?

Almost everything changed.

Djokovic went from a qualifier ranked outside the top 100 to one of the most successful players in tennis history. He eventually won 24 Grand Slam titles, including four US Open crowns, and established himself as a dominant force across all four majors.

His consistency at Grand Slams became one of the defining features of his career. Before the Navone defeat, he had won 78 consecutive opening-round matches at the majors.

That run finally ended in New York.

Novak Djokovic's US Open Defeat Ends The Streak

Against Navone, Djokovic initially appeared on course to preserve his extraordinary record.

He lost the opening set in a tiebreak but fought back to win the next two sets, taking a 2-1 lead. He even held a break advantage in the fourth set.

However, the match gradually turned into a physical battle. Djokovic struggled in the hot conditions and eventually vomited during the contest. He also experienced cramps and required medical treatment before the deciding set.

Navone capitalised on Djokovic's physical decline to win the fourth set 6-2 and the fifth 6-1.

The defeat was Djokovic's first Grand Slam first-round loss since January 2006 and his earliest exit at a major in 20 years.

It also marked his first opening-round defeat at the US Open and ensured that one of the most remarkable streaks in men's tennis had finally come to an end.