Wimbledon begins again 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 draw, as well as offering some of their picks for the best matches of the tournament’s 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 (seven of them 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, an Australian who was born and grew up in the U.S. state of 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 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.
Serena and Venus Williams are reuniting at Wimbledon
Ava Wallace
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 victories over current Queen’s champion Donna Vekić, Wimbledon’s 2022 winner Elena Rybakina and top-10 player Elina Svitolina this month alone.
If the kids aren’t up to the task, Williams may have to take on 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.
In the doubles, Serena and sister Venus, 46, will face Camila Osorio of Colombia and Argentina’s Solana Sierra, neither of them a doubles specialist, in the opening round. 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 men’s singles at this tournament. That didn’t matter at the French Open last month — 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 in the second round. 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 Wimbledon champion. Even at 39, Djokovic’s expertise on grass is unmatched, even if he may not have the fitness to prevail over a two-week tournament anymore. Sinner won’t face him until the semifinals, if the Serbian 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 to try. 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 against Fabio Fognini in round one at this same event last year? That got uncomfortable for a while, even if Alcaraz prevailed.
Sinner, who hasn’t played since Paris, 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 within the tournament. 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-round draws, which are more important on SW19’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 build up that rhythm, and with it her chances of finally getting to a Wimbledon semifinal — she’s been to the last eight there just once, in 2023, and hasn’t made it past the second round since.
She eschewed the warm-up tournament in Bad Homburg, Germany, that she usually plays just before Wimbledon, and which she won last year. Instead, she’s taking this week to acclimate to the courts at the All England Club. Pegula could face the young, rising fellow American Iva Jovic 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 over 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 the 24-year-old gets past her, she’s got a good chance in the quarterfinals with a potential matchup against former Wimbledon champion Rybakina, who has been struggling with her forehand and hasn’t had great results over the past month.
Coco Gauff is attempting to win her first match on grass since 2024. (Susan Mullane / USA Today)
What about Djokovic’s quest for a 25th Grand Slam title?
Djokovic’s luck in the draw has deserted him when he needed it most.
He isn’t the only giant of the sport in the main brackets at Wimbledon this year, 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 recent French Open, where, at 39, his ability to thrive over 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 champion.
He could face either No. 12 seed Andrey Rublev or his own conqueror at the French Open, 24th-seeded Joao Fonseca, in the fourth round. Should he survive that, No. 3 seed Félix Auger-Aliassime, who will surely be ultra-determined at Wimbledon after letting a big opportunity at the French Open slip through his fingers, may await in the quarterfinals.
Ava Wallace’s matches to watch:
Jeļena 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 Świątek has a tricky-looking opener against Taylor Townsend, who won the women’s doubles at Wimbledon a couple of years ago, and likes to play with sharp angles and get to the net. Should Świątek get through that, she would be up against either former world No. 1 and 2021 Wimbledon runner-up Karolína Plíšková or 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 Wimbledon champion Serena Williams, or Eala, who’s been in good form on the grass the last few weeks.
Recent French Open winner 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 Barbora Krejčíková — this event’s 2024 champion and one of the dangerous floaters in this draw everyone was hoping to avoid.
Barbora Krejčíková is a nightmare opponent for any top player. (Ben Stansall / AFP via Getty Images)
Aryna Sabalenka, the world No. 1 but still without a grass-court title to her name, has a similarly tricky first week.
After opening up against qualifier Teodora Kostović, she is slated to face the extremely awkward Oleksandra Oliynykova, whose loopy moonball groundstrokes could be a nightmare for her, as she 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 match against the great home hope Emma Raducanu, or always dangerous former French Open champion 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 she wants to prove a point to get her to really lock in. That was the case at this year’s French Open, where Sabalenka’s best performance by far came against Naomi 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 — which this time a year ago would have been the world No. 5 taking on the world No. 4.
It’s as strong a first-round men’s match as we’ve had in recent memory, and it’s only happening because of Draper’s rotten luck with injuries over the past 12 months or so, which has left the Brit unseeded at Wimbledon. It’s a terrible draw for both players — 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.
That encounter sets the tone for a quarter packed with dangerous players.
Frances Tiafoe, the No. 17 seed who beat Fritz in the Halle Open final at the weekend, is in 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, against this year’s winner of that same event, 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 world No. 37 Alexander Blockx — assuming he has recovered from the ankle injury he suffered in Paris. Blockx is one of few potentially 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 forward to? Let us know in the comments.
