5 women who defeated World No. 1 and World No. 2 to win maiden Grand Slam ft. Madison Keys, Venus Williams

Madison Keys has joined the likes of Venus and Serena Williams in a unique club with her triumph at the 2025 Australian Open. The American finds herself amongst a handful of players who have defeated World No. 1 and World No. 2 to win their maiden Grand Slam.

Winning a Grand Slam can be a mighty task, let alone having to beat the two best players in the world on the way. In Keys’ case, the two opponents were Aryna Sabalenka and Iga Swiatek.

But before we take a look at how the American mastered the two, let’s quickly rewind and look at some of the other women to have achieved the same feat since Serena Williams in 1999:

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Serena Williams at the 1999 US Open

Martina Hingis and Serena Williams at the 1999 US Open. (Source: Getty)

The 1999 US Open final was iconic for more than one reason. Mostly, however, it announced the arrival of Serena Williams and ushered in what would turn into an entire era of power-driven tennis.

Williams, with her fierce serve and groundstrokes, blitzed through the early couple of rounds before scoring fighting wins over big names including Kim Clijsters, Conchita Martinez, and Monica Seles to make the semifinal.

That is when the American, still a teenager, ran into World No. 2 Lindsay Davenport. She was able to come through a topsy-turvy three-setter before taking out World No. 1 Martina Hingis in a more decisive two-set win in the summit clash.

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Venus Williams at the 2000 Wimbledon

Venus Williams at the 2001 Wimbledon Championships. (Source: Getty)

Venus Williams followed in her sister’s footsteps by lifting her maiden Grand Slam trophy at the 2000 Wimbledon Championships. And much like her sister, wins over World No. 1 Martina Hingis and World No. 2 Lindsay Davenport were in the mix.

The American took a three-set victory over Martina Hingis in the quarterfinals before running into sister Serena in the next round. She was able to master the clash of the sisters too, finding herself in the final against Davenport.

Venus Williams was the braver of the two players, hitting bigger and winning the important points to capture the first of her five Wimbledon titles with aplomb.

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Jennifer Capriati at the 2001 Australian Open

Jennifer Capriati at the at 2001 Australian Open. (Source: Getty)

Melbourne has seen a talent take out the World No. 1 and 2 in the final and semifinal to win their maiden Grand Slam title in the past. Jennifer Capriati did it back in 2001.

Capriati, who, much like Madison Keys, was seeded outside the top-10, fought her way into the semifinals where she was up against World No. 2 Lindsay Davenport. She, however, seemed to have played herself into fine form as a straight-sets win saw her move into the final.

Capriati had never made a Grand Slam final before but the occasion hardly seemed to have overwhelmed her. She showed nerves of steel and raced to the finish line against World No. 1 Martina Hingis to capture the trophy.

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Justine Henin at the 2003 French Open

Justine Henin and Kim Clijsters at the 2003 French Open. (Source: Getty)

The turn of the century was a busy time for the Williams sisters, only this time, Serena Williams was on the losing side of an iconic run. Justine Henin was the fourth seed coming into the 2003 French Open but her dogged brand of tennis was always destined for success on clay.

The Belgian made the semifinals having had to break little sweat but needed to conjure up all her strength to outlast Serena Williams in a three-set marathon.

Henin then found herself taking on compatriot and World No. 2 Kim Clijsters in the summit clash. She, however, proved to be too strong for her opponent, taking the famous win for the loss of just four games.

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Madison Keys at the 2025 Australian Open

Madison Keys and Aryna Sabalenka at the 2025 Australian Open. (Source: Getty)

Madison Keys’ runs at the 2025 Australian Open will rank right up there with the very best as she was made to work hard for it. Iga Swiatek and Aryna Sabalenka have dominated the Grand Slam stages in the last few years and beating both of them is no mean feat.

The fact that both Swiatek and Sabalenka play completely opposite brands of tennis makes the American’s fighting victories over them in back-to-back matches even more impressive.

Keys was able to adapt her game, going from control aggression against Swiatek to big serving and free swinging against Sabalenka with the flip of a switch. She even fended off a match point against Swiatek and was fearless in the decider against Sabalenka, earning herself a memorable trophy.