Tearful Novak Djokovic suffers stunning first-round upset for the first time in 20 YEARS to unseeded US Open challenger after horrifying on-court illness

Novak Djokovic has been knocked out of the first round of the US Open in his earliest exit at a Grand Slam for over 20 years, after his body broke down due to a health condition he has struggled with for much of this year. 

Not since the 2006 Australian Open has the Serbian serial champion fallen at the first time of asking at a major, and decades later, Djokovic did so against unseeded world No49 Mariano Navone, 6(5)-7, 7-5, 6-4, 2-6, 1-6.

At this year’s first Grand Slam, Djokovic featured in the final, pinching a set off eventual winner Carlos Alcaraz, but nine months on, Sunday night’s result will undoubtedly call into question how much longer the world No5 can continue to fight at the very top of the sport. 

With the absence of world No1 Jannik Sinner due to injury and Alcaraz playing his first match since April in New York after significant time-out himself, Djokovic's name had been among those who might have capitalised an open draw Stateside. Instead, he will drop out of the top 10 for the first time since 2018. 

3-1 down in the fifth set, in the match's fifth hour, Djokovic appeared moved to tears. A record-breaking 25th Grand Slam may have never seemed further away. 

Against Navone, a gritty clay-court specialist hell-bent on stretching the points for as long as possible to push Djokovic to the brink, everything was difficult. At four hours and 37 minutes, this was the longest first-round match of the 24-time Grand Slam winner’s career, and from the very start, he struggled.

In the immediate aftermath, Djokovic admitted that he 'despised' every moment spent on court as he continued to cite the unnamed issue as a major factor in his body breaking down. 

'It is something that I've been carrying, unfortunately, pretty much every match this year,' Djokovic said, referencing the 'health condition' he first mentioned this month after his defeat at the Cincinnati Open. 

'Vomiting, throwing up, serious issue there, and then my whole body starts to collapse, basically cramping and pain, and the back just gave up in the end, and shoulder, and I couldn't close it out.'

When asked if he thought he could fix it, Djokovic could only manage: 'I don't know. I'm trying, man. I'm trying. Let's see.'

As in Ohio, Djokovic again vomited multiple times during the third set in Flushing Meadows.  

He was in the sixth game when he was overcome with the issue, bent double at the back of the court as he voided his stomach. 

Despite throwing up again during the game, the 39-year-old held his serve, and went on to win his second consecutive set, after dropping the opener during an uncharacteristically error-strewn tiebreak. 

During the opening stages of the match - before the Arthur Ashe Stadium roof was closed due to rain - Djokovic was quickly unhappy in the humid New York evening, rubbing his head with an ice bag and at times clutching his temples as if affected by a headache. 

In one of the early breaks in play, Djokovic hurried the supervisor to turn the air conditioning on when the roof was closed. 

When play restarted, Djokovic took two tablets given to him by a tournament physio as he continued to grapple with his fitness in the early stages. 

Deep in the third set, Djokovic also took on fluids shared with him by his team seated courtside, his camp attempting to find a solution as the match ticked towards its fourth hour. 

Higher up in the stands, Djokovic's wife Jelena looked desolate as her husband battled both his opponent and his own body, at times putting her head in her hands as she watched the match play out. 

Djokovic later admitted that he did consider retiring due to his physical complaints, but winning the second and third sets had brushed aside the possibility.  

After his defeat in Cincinnati to another Argentine, Thiago Agustin Tirante, Djokovic revealed that in recent years he had struggled with the heat more than ever after developing a health condition that has affected him 'for the past couple of years'. 

Post-puking in New York, Djokovic at first appeared to regain his footing in the match as he saw out the third set, and claimed an early break in the fourth.  

But the Argentine proved he was down but not out with an immediate break-back which left Djokovic shaking his head in disbelief. 

After stopping the rot, Navone went on a tear, shutting Djokovic out of the set to force a decider and take the match towards hour five. 

Before starting the fifth set, Djokovic took on more tablets and received a medical timeout, with a US Open trainer massaging the 24-time Grand Slam champion's lower back before he stepped out once again onto the tournament's show court in a fresh white shirt. 

But the final set was a swift one as Djokovic unravelled at pace, at times looking visibly emotional as chances for one final miraculous comeback slipped from his grasp.