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3 Qualifiers Who Could Shock the Draw at Wimbledon 2026

Three qualifiers have strong grass-court credentials and recent history to draw upon for an inspired run.
Robin Montgomery is a qualifier to watch at the 2026 Wimbledon Championships.
Robin Montgomery is a qualifier to watch at the 2026 Wimbledon Championships. | IMAGO / Orange Pictures

In the Open Era, only three women have made the quarterfinals or better at Wimbledon after coming through the qualifying stages: Alexandra Stevenson (1999), Kaia Kanepi (2010), and Lulu Sun (2024).

However, after the surprise run by Maja Chwalinska at the French Open a few weeks ago, the 16 players who battled through the pre-tournament at Roehampton to make the Wimbledon draw this year will surely be even more motivated by that recent feat.

Here’s a look at three to watch out for as the most prestigious tournament of them all gets set to kick off. Catch them while you can, or perhaps, in this new Chwalinska world, you might still see them by the end of the fortnight.

Robin Montgomery

After shooting up the rankings, the 21-year-old from the DMV was forced off the court for nearly a year due to a right wrist issue that required surgery. Returning to the court this March for the first time since last year’s Wimbledon, Robin Montgomery has been grinding her way back up the standings, culminating with her first career WTA title in the Netherlands on grass just a few weeks ago.

She came through the qualifying rounds there, and, counting her Roehampton run, has won 10 straight matches on the surface. Montgomery has a great chance to punch a hole in the draw from the start as she faces the slumping Jasmine Paolini—a Wimbledon finalist two years ago—in the opener.

Bianca Andreescu

One of the most accomplished Grand Slam qualifiers of all time, the 2019 U.S. Open champion is making her first main draw appearance at a major since 2024. Canadian star Biana Andreescu, who has been steadily working her way back up the rankings after being plagued by injuries and loss of form the past few years, does have some grass-court bona fides.

A two-time finalist on the turf, Andreescu—who opens against Shuai Zhang—has the game to hit a lot of players off the court, and will be match-tough coming into SW19.

Ashlyn Krueger

Over the past few weeks, American Ashlyn Krueger has had a jolly old time across the grass courts in England. Including qualifying rounds, Krueger has gone an impressive 13-1 on the turf, with a title-winning run at the WTA 125 stop in Ilkley among those results.

As she’s hovered around the top 100 this year, the former world No. 29 could give her rankings push a major boost at the All-England Club. She kicks things off with one of the most popcorn-worthy first-rounders this year, facing the 31st seed Donna Vekic—a recent Wimbledon semifinalist and this year’s Queen’s Club champion.

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Van Sias
VAN SIAS

Van Sias has covered the professional game for more than a decade. His work has appeared at TENNIS.com, Rolling Stone, The Atlantic, The New York Times and Racquet, among others, and he’s been a featured guest on NPR programs discussing topics ranging from the US Open to the impact of Serena Williams’ retirement. Tennis has long been a part of Van’s life, from playing as a junior in Alabama to currently captaining USTA teams in New York. You can reach him at siasorama@gmail.com.