By STEPHEN WHYNO AP Sports Writer
NEW YORK — Novak Djokovic grinded through physical and internal ailments, made one mistake after another and could not find what it took to beat a feisty, younger opponent who was not intimidated under the lights against tennis’ most decorated player.
The 39-year-old is out of the U.S. Open after a first-round defeat to Mariano Navone on Sunday night, losing, 7-6 (5), 5-7, 4-6, 6-2, 6-1, in a five-set marathon that lasted 4 hours and 36 minutes. It was the longest opening match of a Grand Slam in Djokovic’s career and became his earliest exit in one in two decades, dating to the 2006 Australian Open. He had never lost in the first round at the U.S. Open.
“I didn’t enjoy myself,” Djokovic said. “I think it was obvious that it was an awful feeling on the court for me.”
The record holder with 24 major titles threw up at least once and later appeared to be cramping when he grabbed at his left foot. Djokovic swallowed pills brought to him by a doctor and had his lower back massaged during a medical timeout between the fourth and fifth sets, and he grimaced after several shots.
Djokovic made 70 unforced errors in a painful performance that ended mere minutes before midnight.
“It’s something that I’ve been carrying, unfortunately, pretty much every match this year: vomiting, throwing up, a serious issue there,” Djokovic said. “Then my whole body starts to collapse, basically cramping and pain. Yeah, the back just gave up in the end and shoulder, and I couldn’t close it out.”
With this defeat, 21 years to the day of his U.S. Open debut, the question now lingers as to whether this was Djokovic’s final match at this or any Grand Slam. After the loss, he said he was “trying to address really what’s going on and how far I can go this way.”
It was clear Djokovic was not himself, and the wear and tear of sickness and soreness took its toll. The No. 4 seed from Serbia cruised to early 3-0 and 4-1 leads before blowing them and losing the first set – the first time that happened to him in the first round of the U.S. Open since ’06.
“Just struggled all the way since the fourth game of the match,” Djokovic said. “When it comes to match itself and overall feeling of how I felt with body and playing, it was really not enjoyable. I pretty much despised every moment that I spent on the court for that.”
With his wife, Jelena, watching from the stands with worried looks on her face, Djokovic had moments where he looked like one of the best to play the sport. His fist pump was reserved after winning the second set, and he put his hand to his ear and gestured to the crowd for applause on the way to taking the third.
But Navone – a 25-year-old from Argentina who earlier this year won his first ATP singles title – did not go away.
Neither did the frustration of not being healthy or at his best. After firing a shot wide in the fourth set, Djokovic landed awkwardly and dropped his racket.
Djokovic all but conceded the fourth set. But he was unable to muster enough for the what would have been his 43rd career five-set victory as Navone picked up his first, calling it a dream come true.
“(It) was very tough for me because you are playing with the ‘GOAT’ on this court,” said Navone, who idolized Djokovic growing up. “For sure it’s the best thing I’ve had on court. This is an amazing court and the biggest stage. It’s amazing, the way we play. I mean, five sets. … I’m very happy. I don’t know. What can I say?”
It extended a nightmare stretch for Djokovic, who also lost in the first round at the hardcourt tune-up in Cincinnati earlier this month. That was his first action since losing to top-ranked Jannik Sinner in the semifinals at Wimbledon.
Djokovic expressed hope Saturday that his early exit at Cincinnati gave him more time to prepare for the U.S. Open but acknowledged concern that the first match at any tournament has become challenging for him in recent years. Instead of overcoming the hurdle and building from there, he is left to contemplate an uncertain future.
VENUS OUSTED
Venus Williams bowed out of her 26th U.S. Open singles appearance late Sunday night, falling in straight sets to fellow American wild card Sofia Kenin after not getting on the court until midnight ET.
The 46-year-old lost, 6-2, 7-6 (6), in what could be the final singles match at a Grand Slam, if not her illustrious career. It was Williams’ 15th consecutive singles defeat dating to her last victory in Washington in July 2025.
Williams has now lost six in a row at the U.S. Open since winning in the first round in 2019. With doubles coming up later this week with sister Serena, Venus was not ready to contemplate her future in tennis.
“I don’t think I should have to,” Williams told a small group of reporters after the match. “My mind is fully focused on that: how I recover from this completely insane evening and get ready for the next one.”
Williams and her 27-year-old opponent waited extraordinarily long to take the court at Arthur Ashe Stadium, delayed by Djokovic’s marathon match that threatened to move them next door to Louis Armstrong Stadium. The men’s match ended just in time to play on Ashe – but not before making some history.
At 12:13 a.m., it was the latest start to a match at the U.S. Open, six minutes later than the previous record of Aryna Sabalenka against Ekaterina Alexandrova in the Round of 32 in 2024.
“It’s not ideal,” Williams said. “I would have preferred something else, definitely. It wasn’t great for either of us, so I think we both tried our best.”
Kenin needed just 32 minutes to win the first set, but Williams took advantage of mistakes and made some shots in the second that gave the late-staying crowd reason to cheer, rallying from down 4-2 to force a tiebreak before losing several set points and striking the ball into the net to end it.
“Venus obviously was playing some amazing tennis,” Kenin said. “I just tried to keep fighting. I didn’t feel 100% game-wise, some nerves, but I tried to do the best to stay strong in those moments.”
Concluding at 2:01 a.m., it became the latest finish for a first-round match in U.S. Open history. It is the third-latest for a women’s match at any stage of the tournament.
“I had a lot of great moments,” Williams said. “As the match progressed, I just kept pushing myself to try to find my best tennis and to find my rhythm. It’s not easy to do in the first round. It’s not easy to do at 1 or 2 a.m. in the morning to try to find your rhythm and play your best, but I tried my best.”
Williams is a quarter-century removed from her second of back-to-back championships in New York. She also won Wimbledon five times from 2000-08 to give her seven Grand Slam singles titles.
She attempted to enjoy the experience Sunday night into Monday as much as possible, though she was mostly worried about her on-court play.
“I always try to appreciate it, but it is definitely all business and there’s no room for error,” Williams said. “Try to soak it in, and soaking it in is more fun when the ball’s going in.”
PEGULA, KOSTYUK AMONG WINNERS
Nearly 12 hours earlier, third-seeded Jessica Pegula again experienced the benefits of the Sunday start that began last year.
“It is a little bit weird, but I did kind of enjoy that I could breathe for the next couple of days and everyone else is still freaking out about whether they’re going to win their first round,” she said.
Djokovic later experienced the downside.
“We were just talking about it, and I said, it’s so nice to play on Sunday when you win. But if you lose it’s not nice, because you feel like the tournament didn’t even start and you’re out of it,” No. 11 seed Marta Kostyuk said.
Pegula and Kostyuk both won easily and now the get the benefit of any extra day of rest before returning for the second round, where Pegula will play Kenin.
Pegula leads the women’s tour with 46 wins this season. She has two titles and has reached three other finals. Pegula can take over the No. 1 spot in the rankings if she wins her first major title and No. 2 Elena Rybakina loses before the semifinals.
The 11th-seeded Kostyuk beat Storm Hunter, 6-4, 6-1, for a strong start to the year’s final major after reaching the semifinals at the French Open and Wimbledon.
MEDVEDEV WINS, DEFENDING CHAMPS PLAY MONDAY
Some of the biggest headliners don’t begin until Monday. Two-time defending champion Aryna Sabalenka plays her opening match against Camila Osorio, before Carlos Alcaraz, who won his second U.S. Open title last year, plays his first singles match since April after recovering from a right wrist injury.
Past U.S. Open champions Naomi Osaka, Iga Swiatek, Sloane Stephens and Stan Wawrinka are also on the Monday schedule, along with Wimbledon women’s champion Linda Noskova and men’s contenders such as Ben Shelton, Arthur Fils, Felix Auger-Aliassime and Frances Tiafoe.
Daniil Medvedev, the 2021 U.S. Open champion, shook off his miserable preparation for the tournament by beating Hugo Gaston, 6-4, 6-2, 6-4. The No. 7 seed was just 1-3 so far in the North American hard-court swing, usually a time he thrives.
“Last couple of weeks was not easy,” Medvedev said. “But I’m happy that today I managed to produce high-level tennis.”
RAIN CAUSES HAVOC
Other winners Sunday included No. 9 Elina Svitolina, No. 19 Jasmine Paolini and No. 31 Leylah Fernandez, the 2021 U.S. Open runner-up. No. 27 seed Barbora Krejcikova, a two-time Grand Slam singles champion, lost to Kamilla Rakhimova, 7-6 (4), 6-2.
American Tommy Paul, the No. 20 seed, bounced back from losing a first-set tiebreak to Coleman Wong to win, 6-7 (3), 6-1, 6-3, 6-3. Wong a year ago became the first man from Hong Kong to win an Open-era Grand Slam men’s singles match on the way to reaching the Round of 32.
Seven matches couldn’t be completed because of rain – and one was delayed even though it was being played in the other stadium with a retractable roof. There was a mechanical issue with one of the sensors at Louis Armstrong Stadium, and even after the roof finally closed, the court had to be dried before No. 15 seed Alexander Bublik beat J.J. Wolf.
Maric Cilic, the 2014 U.S. Open champion, and 2022 runner-up Casper Ruud both withdrew with injuries.
TOURNAMENT GETTING A NEW LOOK
Though the main draws didn’t begin until Sunday, action at the U.S. Open has already been going on for nearly a week. Large crowds gathered for the mixed doubles tournament, an exhibition headlined by Roger Federer’s return to Flushing Meadows and the singles qualifying tournaments, with admission to the grounds free.
Fans who came for the first time Sunday might have noticed a tournament in transition. The U.S. Open is in the second year of a three-year renovation of Arthur Ashe Stadium, the main venue at the USTA Billie Jean King National Tennis Center. The improvements in the $800 million project include the addition of some lower-level seating, upgrades and additions of entertainment areas and the construction of a player performance center.
“Please pardon our appearance while we are reimagining spectacular,” reads a sign above the entrance to Ashe.
The project is scheduled to be completed in time for the 2027 U.S. Open.