US Open 2026 Underdog Stories: 5 Shocks From Week 1

 

US Open 2026 Underdog Stories: 5 Shocks From Week 1

The US Open 2026 underdog stories stacked up fast. Novak Djokovic, seeded on the strength of a world No. 5 ranking, lost a Grand Slam first-round match for the first time in his career. A British qualifier ranked outside the top 200 punched through against a seed. And a former champion came back from a broken foot on a wild card.

That's three storylines before most of the seeds had even hit a ball. The tournament runs August 30 through September 13, 2026, with a record $108 million purse and $5.5 million for each singles champion (as of September 1, 2026). Here's what actually happened, and which of these runs I think has legs.

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Djokovic's exit is the biggest of the US Open 2026 underdog stories

Novak Djokovic, 39, lost to Argentina's Mariano Navone 7-6(5), 5-7, 4-6, 6-2, 6-1 on August 31, 2026, in a match that ran 4 hours and 35 minutes. It was the first time in his career he had gone out in the first round of a Grand Slam, and it ended a run of 78 consecutive first-round wins going back to 2006.

The scoreline tells you where it turned. Djokovic took the opening set in a tiebreak, then dropped the next three, and by the end Navone was winning 63.3% of the points across the last two sets, per CBS Sports. Seventy unforced errors from a player who has built two decades on not missing.

Navone, for his part, played the match of his life against a 24-time major champion on Arthur Ashe. Nobody had that on a bracket.

Why did Novak Djokovic lose in the first round?

Djokovic was physically compromised. He vomited courtside several times during the match against Mariano Navone and said afterward that the stomach trouble had shown up in nearly every match he'd played this year, according to Yahoo Sports. He also said a return to New York next year now looks less likely than not.

That last part is the line that turned a result into a news cycle. He didn't announce a retirement. He said the odds had moved.

I'd take him at his word on the health and stay skeptical on the retirement talk — players say that in the tunnel at 1 a.m. after five sets and feel different in February. But 39-year-olds who spend a match being sick between points don't usually get faster.

Sinner's withdrawal cracked the men's draw open

World No. 1 Jannik Sinner withdrew from the 2026 US Open on August 21, 2026, with a right knee injury, ESPN reported. He came in at 44-3 on the season and as the 2024 champion in New York, so his absence removed the most likely title winner before the first serve.

Two things follow from that. The obvious one: somebody else lifts the trophy. The less obvious one: every player in the bottom half of the draw suddenly has a path worth taking seriously, which is exactly the condition that turns a decent qualifier into a story.

Harry Wendelken and Britain's best qualifying week since 1988

Harry Wendelken, a 24-year-old British qualifier with a career-high ranking of No. 223 (as of April 13, 2026), beat 14th seed Vilius Gaubas 6-7(3), 7-6(5), 7-6(5) in the final round of qualifying to reach his first US Open main draw. Three sets, two of them tiebreaks, after losing the first.

He wasn't alone. Harriet Dart, Toby Samuel and Francesca Jones all came through the same qualifying event, making four British players in one Grand Slam qualifying field — something that hadn't happened since the 1988 Australian Open, per the LTA.

Qualifying is three matches in four days on outside courts with maybe 200 people watching. Winning the last one from a set down, against a seed, is my favorite kind of tennis result: no cameras, no rankings points to protect, just somebody refusing to lose.

The wild cards: Sloane Stephens and Venus Williams

Sloane Stephens, the 2017 US Open champion, got a main-draw wild card announced on August 18, 2026, after a stress fracture in her right foot kept her out for seven months in 2025.

She has climbed from No. 1,098 at the start of the season to No. 240. In Cincinnati she beat Anastasia Potapova for her first top-30 win since Madrid in 2024, according to the WTA.

Venus Williams, 46 and a two-time champion here, took a wild card too. She's ranked No. 621 and arrives on a 14-match losing streak.

Those two wild cards get discussed as one thing, and I don't think they are. Stephens is 33 with a ranking that has moved 858 places in one season — that's a comeback with a number attached. Venus is playing on a different clock entirely, and the appeal is the appearance, not the draw.

Story	Player	Background	Key number
First-round upset	Novak Djokovic (No. 5)	Lost in 5 sets, 4h 35m	78-match first-round streak over, 70 unforced errors
Withdrawal	Jannik Sinner (No. 1)	Right knee injury	Out August 21, 2026; 44-3 on the season
Qualifier	Harry Wendelken (GBR, 24)	Beat the 14th seed in 3 sets	Career high No. 223; 4 British qualifiers, first since 1988
Wild card	Sloane Stephens (2017 champ, 33)	7 months out with a foot fracture	No. 1,098 to No. 240
Wild card	Venus Williams (2-time champ, 46)	Comeback appearance	Ranked No. 621, on a 14-match losing streak

There was one more result worth flagging: reports out of the first round had No. 92 Kamilla Rakhimova beating No. 29 Barbora Krejcikova, though I've only seen that in one outlet so far, so treat it as unconfirmed until the official draw sheet catches up.

FAQ

Why did Novak Djokovic lose in the first round of the 2026 US Open?

He was struggling physically through a 4-hour, 35-minute match, vomiting courtside and dealing with cramping and back pain, and Mariano Navone took the last two sets comfortably. Djokovic said the stomach problem had affected almost every match he played in 2026.

Who is Harry Wendelken?

He's a 24-year-old British player from Cambridge with a career-high ranking of No. 223 (as of April 13, 2026). He reached the 2026 US Open main draw by beating 14th seed Vilius Gaubas in the final qualifying round after dropping the first set.

Is Sloane Stephens playing in the 2026 US Open?

Yes. The 2017 champion is in the main draw on a wild card announced August 18, 2026, after returning from a right foot stress fracture that cost her seven months. Her ranking has recovered from No. 1,098 to No. 240 this season.

Why is Jannik Sinner not playing the 2026 US Open?

The world No. 1 withdrew on August 21, 2026, saying his right knee needed more recovery time. He was 44-3 on the season and defending a title he won here in 2024.

What I'd watch next

Five days in, the US Open 2026 underdog stories have already outrun the preview pieces written before the tournament started. Djokovic's exit is the headline, but the Wendelken run is the one I'd keep an eye on through the second week of the draw.

Watching for the rest? Keep the Stephens result column open. A player who was outside the top 1,000 in January doesn't need to win the thing to have won her year.