Madison Keys celebrates her only game win against Aryna Sabalenka during the WTA semifinals at the BNP Paribas Open in Indian Wells, Calif., Friday, March 14, 2025.

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Fiery Anna Kalinskaya Topples 2nd Seed Madison Keys in Charleston Open 2025 Round of 16

Kalinskaya earns first Top-10 win in close to a year.

Madison Keys celebrates her only game win against Aryna Sabalenka during the WTA semifinals at the BNP Paribas Open in Indian Wells, Calif., Friday, March 14, 2025.

In the upset of the tournament so far, Anna Kalinskaya dumped second seed Madison Keys out of the Charleston Open WTA-500 event on Thursday. The 14th seed had nearly 76% first serves in play, and saved 7/8 break points for a 6-2 6-4 victory. Kalinskaya will now face Sofia Kenin in the quarterfinals – Kenin overcame Daria Kasatkina in her Round of 16 battle.

Kalinskaya was coming into the match on the back of a comfortable win in Round-2. She beat Caty McNally, whom she had partnered up with at both Indian Wells and Miami. Yet, nobody expected her to pull off the mammoth upset against Keys. The 26-year-old has seen a massive fall in her ranking owing to a dip in form, and will want to make amends this week.

Madison Keys Has No Answers to Anna Kalinskaya in Charleston Open R16

Keys opened the match with a rollicking forehand winner down the line, exciting the fans for what’s to come. Despite using her serve plus one tactic to good effect early on, the reigning Australian Open winner was broken from 40-0 up in game three. Noticing that Keys isn’t the most comfortable on clay, Kalinskaya opted for multiple drop shots to take control of the match 6-2.

When Keys nailed a passing shot in the beginning of the second set, there were ominous signs of a potential shift in momentum. But Kalinskaya was able to douse the fire in no time – going toe-to-toe with the 30-year-old Rock Island native from the back of the court. And despite producing an inside out as well as inside in forehand winner to save two match points, it was too little too late for ‘Madi’.

Anna Kalinskaya forced a backhand error from the American to claim a relieving 6-2 6-4 win in the first night session encounter on Credit One Stadium.

Kalinskaya in Seventh Heaven After ‘Special’ Win

The lacklustre performance from the World No. 5 meant that Kalinskaya achieved her first Top-10 victory in over ten months, and her 11th overall. Keys hit 40 unforced errors and won less than 50% of her first serve points, meaning that her Russian counterpart equalled their head to head at 1-1. After the match, the former World No. 11 emoted what this Charleston upset meant to her.

Anna Kalinskaya after beating Madison Keys in Charleston

“This one is special. I needed this for my confidence. I had an unfortunate start to the year. It’s nice to be back and playing at such a high level.” ❤️

pic.twitter.com/rim4OYlfLf
— The Tennis Letter (@TheTennisLetter) April 3, 2025

“This one is special, I needed this for my confidence,” she said. “I had an unfortunate start to the year, but it’s been nice to be back and playing at such a high level.” Kalinskaya also revealed the vital change of plan which helped her. “I think the key tonight was to change the rhythm a little bit; I did a few drop shots, especially in the first set.”

Kalinskaya now faces the uphill task of beating a third American in a row, in the form of former Australian Open winner Sofia Kenin. Catch all the WTA Charleston Open 2025 quarterfinal action on Friday.

Anna Kalinskaya

Australian Open

Charleston Open

Madison Keys

Miami Open

Tennis

WTA

Sankalp Harikrishnan

A passionate sports fan through and through, I am currently pursuing my MA in Global Sports Journalism. I specialise in tennis and football writing at The Playoffs News, and I have prior experience working at EssentiallySports and Sportskeeda. Born and raised in Bengaluru, India, sport was my safe space right from my childhood. After trying my hand at multiple sports and representing my educational institutions in cricket, badminton and table tennis, I found sports media to be my calling.