Jun 1, 2023; Paris,France; Madison Keys (USA) prepares to return a shot during her match against Kayla Day (USA) on day five at Stade Roland-Garros.

tennis

Madison Keys vs. Anna Kalinskaya Head to Head Record, Preview and Prediction for WTA Madrid Open 2025 Round of 32

Powerhouse face-off on Super Saturday.

Jun 1, 2023; Paris,France; Madison Keys (USA) prepares to return a shot during her match against Kayla Day (USA) on day five at Stade Roland-Garros.

In a repeat of the 2025 Charleston Open R16, Madison Keys battles Anna Kalinskaya in Round-3 of the 2025 Mutua Madrid Open on Saturday. Both players are having confidence-boosting seasons. The winner of this match will face either Emma Navarro or Donna Vekic in the Round of 16 in Madrid. Who is going to come out on top?

Madison Keys is the No. 5 seed this week at the Spanish capital. She is the reigning Australian Open champion, and also has a title in Adelaide as well as a semifinal in Indian Wells to back it up. The 30-year-old has a record of 13-4 on clay over the past year. Winning almost 73% of her service games over the past year, Keys’ rise has been awe-inspiring to say the least. She defeated Lucia Bronzetti 6-4 6-3 in Round-2 to book her spot in this match.

A powerful striker of the tennis ball, Anna Kalinskaya recently overhauled Keys on the green dirt of Charleston. Seeded 30th here, the 26-year-old has an underwhelming 4-5 showing on this surface over the past year. Kalinskaya converts 40% break points – which ranks 105th on the WTA Tour – this is an important stat against a strong server like Keys. The Russian star beat Diane Perry 7-6(4) 6-4 in Round-2.

Madison Keys vs Anna Kalinskaya Head to Head Record

1-1 is the current head to head record between Madison Keys and Anna Kalinskaya.

While Keys took the early lead in the duel with Kalinskaya, the former World No. 11 recently returned the favour. Interestingly, both of the meetings between the two players have come on outdoor clay. At the 2022 Roland Garros Championships, ‘Madi’ prevailed in a three-set epic. In Charleston, Kalinskaya put Keys’ running shoes to the test and outlasted her.

Event	Round	Winner	Score
2025 Charleston	Round of 16	Anna Kalinskaya	6-2 6-4
2022 Roland Garros	Round of 128	Madison Keys	6-3 3-6 6-4

Madison Keys vs Anna Kalinskaya Titles Comparison

Madison Keys	Category	Anna Kalinskaya
1	Grand Slams	0
10	WTA Singles Titles	0
0	WTA Doubles Titles	3
1	WTA-1000 Titles	0
SF (Rio 2016)	Olympics Best Performance	–
No. 5	Current World Ranking	No. 29

Madison Keys vs Anna Kalinskaya Madrid Open 2025 Prediction

99 – Madison Keys is now the player with the outright third most wins (99) amongst Americans in WTA-1000 events since the format introduction in 2009. Climbing. #MMOPEN | @MutuaMadridOpen @WTA @WTA_insider pic.twitter.com/jGsvgAfWdH
— OptaAce (@OptaAce) April 24, 2025

In all probability, Keys will take her learning from the Charleston clash and apply it in La Caja Magica. One of the vital improvements she will have to make is her variety – the American was far too one dimensional in her approach. When she opted for a Plan-B, her execution was haywire. Although we do think the Grand Slam winner will come out with newfound hunger and plans, Kalinskaya might edge out another victory.

Prediction: Anna Kalinskaya in three sets.

Madison Keys vs Anna Kalinskaya Madrid Open 2025 Betting Odds

Madison Keys Win: 4/9

Anna Kalinskaya Win: 2/1

Anna Kalinskaya

Aryna Sabalenka

Betting

Iga Swiatek

Madison Keys

Madrid Open

Tennis

WTA

WTA 1000

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.