Wimbledon bracket 2026: Serena Williams’ first match and contrasts for defending champions

Wimbledon begins Monday in London, and the men’s and women’s singles brackets have thrown up some blockbuster first-round matches.

The Athletic’s Ava Wallace, Matthew Futterman and Charlie Eccleshare analyze an intriguing bracket, as well as offering some of their picks for the best matches of the opening days.

What does Serena Williams’ return to singles look like?

Serena Williams got some good luck Friday.

Any 44-year-old legend, with 23 Grand Slam singles titles (and seven at Wimbledon) to their name, is probably pretty happy if their first singles match in just under four years is against a 20-year-old who is 3-15 on the season.

That would be Maya Joint, the 20-year-old Australian who grew up in Michigan. Joint has some grass pedigree — she won the Eastbourne Open, which precedes Wimbledon last year — but her form in 2026 does not represent good preparation for the occasion of facing a titan of the sport on (almost certainly) its most famous court.

It’s possible that Joint is slightly too young to have gotten the full Williams experience, and there will also be the sense of fearlessness that comes with having nothing to lose in the grand scheme of things. But Williams, judging by all the noises she has made during this comeback, is playing with that same belief. She has already won it all. Anything she does now is a bonus.

If Williams can get by Joint, she will likely face 21-year-old Alexandra Eala of the Philippines in the second round. That won’t be easy. Eala has proven to be a proper grass-court player this year and last, with some impressive wins over Queen’s champion Donna Vekić, 2022 Wimbledon champion Elena Rybakina and top-10 player Elina Svitolina this month alone.

If the kids aren’t up to the task, Williams may have to handle defending champion Iga Świątek in the third round. That’s the kind of match the Wimbledon bracket gods were hoping for to open the event, but Williams is probably happier with what came out of the bag Friday morning in southwest London. Let the intrigue begin.

Does Jannik Sinner find himself in a familiar position?

Go ahead, search high and low. It’s hard to find a player who looks ready to stand in the way of Jannik Sinner at the business end of the tournament. That didn’t matter at the French Open — a hugely disciplined performance from then-world No. 56 Juan Manuel Cerúndolo, as Sinner wilted with illness and heat, was enough to knock him out. But the impact of that seismic shock has dwarfed just how handily Sinner was beating Cerúndolo until his body betrayed him.

The biggest obstacle for Sinner is probably Novak Djokovic, the seven-time champion. Even at 39, Djokovic expertise on grass is unmatched, even if he may not have the fitness to prevail over two weeks anymore. Sinner won’t face him until the semifinals, if Djokovic can get that far.

Daniil Medvedev beat Sinner at Wimbledon a couple years ago. Could he do it again? Maybe, but he’d have to get to the quarterfinals. And Medvedev isn’t exactly a banker these days. Ultimately, Sinner’s draw has fallen with no genuine banana skins, the kind of early-round matches that can trip up even the best players in the world. Remember Carlos Alcaraz and Fabio Fognini last year? That got uncomfortable for a while, even if Alcaraz prevailed.

Sinner, who hasn’t played since the French Open, likely would have been fine even if he had faced someone troublesome early. At the moment, it doesn’t look like he will.

Matt Futterman’s matches to watch:

Bianca Andreescu (Q) vs. Zhang Shuai

Serena Williams (WC) vs. Maya Joint

Hugo Gaston (Q) vs. Stefanos Tsitsipas

Alexander Blockx vs. Alexander Zverev (2)

A sunny outlook for the top American women?

Americans always have something to celebrate during Wimbledon because July 4 falls during the fortnight. This year, the three top-seeded American women — No. 4 Jessica Pegula, No. 6 Amanda Anisimova and No. 7 Coco Gauff — have reason to cheer a whole week early.

Pegula, Anisimova and Gauff should be pleased with their early rounds, which are more important on Wimbledon’s grass than at any other Grand Slam, because of the shortness of the season and the lack of time to build rhythm.

Pegula has taken extra care this year to to build up that rhythm, and with it her chances of finally getting to a Wimbledon semifinal — she’s been to the quarters just once, in 2023, and hasn’t made it past the second round since then. She eschewed the warm-up tournament in Bad Homburg, Germany, that she usually plays just before the tournament and which she won last year. Instead, she’s taking the week to acclimate to the courts at the All England Club.

She could face the young rising American Iva Jović in the fourth round and Gauff in the quarterfinals, but those aren’t scary matchups for the 32-year-old, who’s more accomplished on grass than both.

Gauff drew Belinda Bencic as a potential fourth-round matchup but should — emphasis on the should — have time to work her way into the tournament for the first three rounds. Anisimova’s first big challenge could be a fun matchup against fellow big-hitting American Madison Keys in the third round. But if Anisimova gets past her, she’s got a good chance in the quarterfinals with a potential matchup against former Wimbledon champion Elena Rybakina, who has been struggling with her forehand and hasn’t had great results over the past month.

What about Novak Djokovic’s quest for a 25th Grand Slam title?

Novak Djokovic’s luck in the draw has deserted him when he needs it most.

He isn’t the only giant of the sport in the main draw at Wimbledon, thanks to Serena Williams’ return to singles. While sharing the media circus with the 23-time Grand Slam champion may help take some external pressure off of Djokovic, his quest for a history-making 25th Grand slam title will be extremely challenging nonetheless.

He faces the same physical obstacles as he did in the French Open, where at 39 his ability to thrive in five sets clearly waned (though his matches should be speedier on grass) but the real problem is ending up on the same side of the draw as Sinner.

Hurdles for Djokovic also appear long before he’ll even get to think about a semifinal against the world No. 1 and defending champ. He could face either No. 12 Andrey Rublev or his conquerer at the French Open, No. 24 Joao Fonseca, in the fourth round. Should he survive that, No. 3 seed Félix Auger-Aliassime, who will be ultra-determined at Wimbledon after letting a big opportunity at the French Open slip through his fingers, awaits in the quarterfinals.

Ava Wallace’s matches to watch:

Jelena Ostapenko vs. Harriet Dart (WC)

Emma Navarro (23) vs. Paula Badosa

Marin Čilič vs. Daniil Medvedev (8)

Frances Tiafoe (17) vs. Térence Atmane

Early challenges for the women’s favorites?

A few of the biggest names on the women’s side would have been forgiven for taking a deep breath after looking at Friday’s draw.

Defending champion Iga Świątek has a tricky-looking opener against Taylor Townsend, who won the doubles event a couple of years ago, and likes to play with sharp angles and get to the net. Should Świątek win that, she would be up against either former world No. 1 and 2021 Wimbledon runner-up Karolína Plíšková or the fast-rising Czech youngster Tereza Valentová.

Plíšková, an excellent grass-court player, is someone none of the seeds would have relished playing. Emerge unscathed from there and it could be seven-time champion Serena Williams, or Alexandra Eala, who’s been in good form on the grass the last few weeks.

French Open champion Mirra Andreeva opens up against the experienced and tough Magda Linette, a former Australian Open semifinalist. That’s before a projected second-round match against the 2024 Wimbledon champion Barbora Krejčíková, one of the dangerous floaters everyone was hoping to avoid.

Aryna Sabalenka, the world No. 1 still without a career grass-court title to her name, has a similarly tricky first week. After opening up against qualifier Teodora Kostović, Sabalenka is slated to face the extremely awkward Oleksandra Oliynykova, whose loopy moonball groundstrokes could be a nightmare for the world No. 1, who generally likes to play with as much rhythm as possible. Oliynykova has also publicly called for Russian and Belarusian athletes, including Sabalenka, to be banned from competing for not denouncing Vladimir Putin’s invasion of her native Ukraine.

There’s then the potential for a third-round rematch against the great home hope Emma Raducanu, or the former French Open champion and always dangerous Jeļena Ostapenko.

Sabalenka might be helped by having some big names early on. She can be a bit flat in the early rounds, and it sometimes takes a match in which Sabalenka wants to prove a point to get her to really lock in. That was the case at the French Open where by far Sabalenka’s best performance came against Osaka, who was also, in theory, her toughest opponent.

A quarter of death in the men’s draw?

The fourth quarter of the men’s draw starts with Taylor Fritz up against Jack Draper in the first round. A match that this time a year ago would have been the world No. 5 against the world No. 4. It’s as strong a first-round men’s match in recent memory, and is only possible because of Draper’s terrible luck with injuries over the last 12 months or so that have left him unseeded. It’s a terrible draw for both (and the tournament), the kind of match that is theoretically possible for a big name beginning a comeback but one that rarely happens in reality.

The matchup sets the tone for a quarter packed with dangerous players. Frances Tiafoe, the No. 17 seed who just beat Fritz in the Halle Open final, is there and is set to face Alexander Bublik, the No. 10 seed and last year’s Halle champion, in the fourth round. Another projected last-16 match in this quarter is Jiří Lehečka, a finalist at Queen’s 2025, up against this year’s winner Francisco Cerúndolo.

Down at the very bottom is of course the No. 2 seed Alexander Zverev, fresh from his French Open title win. He has a challenging opener against the world No. 37 Alexander Blockx, assuming he has recovered from the ankle injury he suffered in Paris. Blockx is one of few dangerous non-seeded players in the quarter, along with the likes of Gabriel Diallo, Alex Michelsen and Corentin Moutet.

Charlie Eccleshare’s matches to watch:

Yulia Putintseva vs. Tatjana Maria

Taylor Townsend vs. Iga Świątek (3)

Stan Wawrinka (WC) vs. Matteo Berrettini

Taylor Fritz (6) vs. Jack Draper

Wimbledon 2026: Women’s singles draw

Wimbledon 2026: Men’s singles draw

Which matchups are you looking out for? Let us know in the comments.

This article originally appeared in The Athletic.

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