Novak Djokovic, widely regarded as one of the greatest tennis players of all time, has surprisingly never beaten a select group of opponents in competitive matches. Despite holding the record for the most singles Grand Slam titles won by any player, the Serb has come unstuck against seven rivals as he approaches his 40th birthday.
As the 2026 tennis season winds down, a review highlights those players who remain undefeated against Djokovic in their head-to-head encounters.
Recent Grand Slam Upsets
Joao Fonseca, one of the sport's rising stars, faced Djokovic in the third round of the French Open this year and emerged victorious in emphatic fashion, coming from two sets down to defeat the tennis legend.
In the final Grand Slam of the year, Mariano Navone stunned Djokovic in the first round of the 2026 US Open, marking another first-time defeat for the Serb.
More First-Time Defeats
Thiago Agustin Tirante also got the better of Djokovic at the Cincinnati Open earlier this year. After losing the opening set, the Argentine rallied to win back-to-back sets 6-4.
Reilly Opelka, a former wonderkid, did not face Djokovic until 2025, when the pair met at the Brisbane International and the American came out on top.
These results underscore a growing trend of first-time opponents defeating Djokovic in recent years, as his struggles on court have continued.
