5 Grand Slam champions who have winning records against Serena Williams ft. Naomi Osaka, Bianca Andreescu

Serena Williams has been one of the greatest tennis players of all time and her many records are proof that she has proven to be a formidable opponent over the years. The head-to-head record against most players that Serena has contested is therefore heavily in the American's favor.

Even so, there are a few exceptions where the 23-time Grand Slam champion has lost more matches than she has won.

Let's take a look at 5 Grand Slam winners who have winning records against the great Serena Williams.

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#5 Elena Rybakina 1 - Serena Williams 0

Elena Rybakina, who was the 21st seed at Roland Garros last year, ousted the three-time French Open champion in the fourth round.

The 2022 Wimbledon champion appeared calm and composed as compared to Serena, who seemed to be short on confidence during their encounter at Roland Garros.

An inspired performance from the Russian-born Kazakh player saw her through to the quarterfinals with a 6-3, 7-5 victory where she went on to lose to Anastasia Pavlyuchenkova.

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#4 Sofia Kenin 1 - Serena Williams 0

Sofia Kenin's winning moment against Serena at the 2019 French Open

Sofia Kenin accounted for Bianca Andreescu before taking on Serena Williams in the third round of the 2019 French Open.

The American, who was 20 at the time, attacked Serena's serve and tested her senior compatriot with a series of drop shots, winning the first set in a comprehensive fashion.

Kenin, who trained with Rick Macci, won seven straight games in the second set before her opponent managed to hold serve.

Serena attempted a comeback by leading 4-3 but failed to find a way to tackle Kenin's serve, finally going down 6-2, 7-5 against a player who would win the Australian Open the following year.

Kenin went on to lose to Ashleigh Barty in the fourth round at Roland Garros.

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#3 Arantxa Sanchez Vicario 4 - Serena Williams 3

The Spaniard won four matches in a row against the upcoming American star between 1998 and 1999.

Arantxa Sanchez Vicario first beat Serena at the Adidas International in Sydney in 1998 and kept up the winning momentum at the French Open.

A switch to grass made little difference to the results with the 1994 ITF Champion of the Year romping home at Eastbourne before registering her fourth win over the American youngster in Berlin a year later.

A dramatic turnaround followed the same year, with Serena displaying her class to win the quarterfinals at Manhattan Beach and the 1999 Grand Slam Cup before winning the semifinals of the Canadian Masters in 2000.

The three-time French Open champion retired in 2002.

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#2 Bianca Andreescu 2 - Serena Williams 0

Bianca Andreescu ran into Serena Williams for the first time in Toronto when the two clashed in the finals of the 2019 Rogers Cup.

Serena, who was aiming to win her first title of the season, retired after just 19 minutes on court citing back spasms even as the Canadian, who was leading 3-1, went on to become the first player from her country to win the event in half a century.

After going down to Naomi Osaka in the 2018 US Open final, Serena had yet another chance to take a shot at Margaret Court's Grand Slam record in New York a year later.

It wasn't to be, however, as Andreescu, who was then 19, shocked the six-time US Open champion 6-3, 7-5 to become the first Canadian to win a Grand Slam in the Open era.

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#1 Naomi Osaka 3 - Serena Williams 1

Naomi Osaka was on song after winning the Indian Wells Open and began on a strong note against her illustrious opponent during their first-ever meeting in Miami.

The Japanese sensation rattled Serena with a series of strong serves and powerful returns, to which the eight-time champion had no answer to.

Osaka dominated the second set to win 6-3, 6-2 and sounded the warning bells before the duo met for the second time in the US Open finals the same year.

Serena wasn't short on the motivation front as she had her eyes on a 24th Grand Slam title. However, she lost her cool in the face of some persistent high-level tennis from her opponent.

With the crowd firmly behind her, the US legend took on chair umpire Carlos Ramos, calling him a thief after being penalized but fell to Osaka for a second time with the scoreline reading 6-2, 6-4.

Facing her childhood idol for the third time in the quarterfinals of the Roger's Cup a year later, the youngster lost 6-3, 6-4, but beat Serena with an identical scoreline on the big stage when the two met in the semifinals of the Australian Open in 2021.