Charleston holds a special significance for Madison Keys, as highlighted by her statement after winning the title in 2019: “I love this tournament. It’s one of my favorites, every year it’s the first one I sign up for. It feels like home, and coming here is always amazing.” Now, six years later, Keys returns to this event as a Grand Slam champion, having enjoyed a successful 2025 season thus far. She has started her Charleston Open campaign, a tournament she considers her “second home,” with a victory, setting up a Round of 16 clash against Russia’s Anna Kalinskaya. The question remains: can she overcome the challenge posed by former world number 11, Anna Kalinskaya?

Madison Keys vs Anna Kalinskaya: Preview

Madison Keys has already won two titles this season (Adelaide International and the Australian Open). Although she made a disappointing exit from Miami after losing the 19-year-old Filipina Alexandra Eala in straight sets, Keys has managed to get back to winning ways in Charleston.

She defeated her compatriot Caroline Dolehide in just 1 hour and 42 minutes by a 6-3,7-6(4) margin in the previous round.

On the other hand, Anna Kalinskaya has struggled a lot with health issues and injury concerns this season. Kalinskaya was forced to give mid-match walkovers twice this season – in Adelaide and Singapore. However, Kalinskaya did manage to make a comeback at the Middle East swing, but she struggled with her form in the next few tournaments.

However, the 26-year-old Russian has got off to a winning start in Charleston, and she’ll be entering this match against Keys following her 6-1,6-4 triumph over another American, Caty McNally.

Keys vs Kalinskaya: Head-to-Head

Madison Keys and Anna Kalinskaya have crossed paths only once in their careers so far. At the moment, Keys leads the H2H record against Kalinskaya by a very fine margin (1-0).

• 2022 French Open R128: Keys 6-3,3-6,6-4.

Prediction: Keys will win this match in straight sets

Madison Keys (5) has been in better form this season. She has a win-loss record of 20-3, but on the other hand, Anna Kalinskaya (33) has recorded just 5-7 in 2025.

Apart from that, if we take a glimpse at their previous record in this tournament, apart from winning the title in 2019, Keys reached the final here in 2015. Whereas, Kalinskaya’s best result in Charleston came in 2023 when she reached the QF.

Now, if we shift our focus to their playing styles, Anna Kalinskaya is known for her aggressive baseline game, characterized by a powerful forehand and solid backhand, combined with quick footwork and an ability to change directions swiftly. However, the biggest concern for her in this season is that she has hit only 8 aces so far, but committed 26 double faults!

So, keeping things tidy will be extremely crucial for Kalinskaya against the Top 10 opponent.

Madison Keys is known for her aggressive, baseline-oriented playing style that is characterized by a powerful forehand and strong serve, making her a formidable opponent on the women’s Tour. Talking about serves, Keys has already hit 111 aces this season, and other than that, she also loves to dictate the rallies from the baseline.

Looking at her incredible form this season, I think Keys will not only dictate the rallies but also dictate the match against the Russian in this epic R16 clash!