Serena Williams is perhaps the greatest player in the history of women's tennis. The American has excelled in both singles and doubles, winning a total of 125 titles.
In singles, Williams has won 23 Grand Slams, the most in the Open Era. Overall, only Margaret Court has won more Majors than her. She has a total of 16 Grand Slam doubles titles to her name.
For the majority of her career, Serena dominated the women's game at a time when she had to face some exceptional players. The American faced the likes of Venus Williams, Justine Henin, Kim Clijsters, Maria Sharapova, Martina Hingis, and Lindsay Davenport, to name a few. She has a positive head-to-head record against each of them.
However, there have been four players who have managed to fare well against Williams in multiple appearances against her. On that note, let us take a look at the women who have a winning record against Serena Williams.
Note: Only includes players who have played multiple matches against Serena.
#1 Arantxa Sanchez Vicario: 4-3
Former World No. 1 Arantxa Sanchez Vicario is the only player to win three or more matches against Serena Williams and have a positive head-to-head record against her.
The Spaniard faced her for the first time in the semi-finals of the Sydney International in 1998. She beat Serena 6-2, 6-1 to book her place in the final, where she would defeat Venus Williams 6-1, 6-3.
Sanchez Vicario won her next three meetings against the 23-time Grand Slam champion, including a 4-6, 7-5, 6-3 in their only Grand Slam encounter at the 1998 French Open.
However, Serena Williams won her next three matches against the Spaniard, with their last meeting coming in the semi-finals of the 2000 du Maurier Open (now known as the National Bank Open). The American won the match 6-2, 6-4 to reach the final, where she lost to Martina Hingis.
#2 Naomi Osaka: 3-1
Naomi Osaka is one of the few active players who has played multiple matches against Serena Williams and has a positive head-to-head record against her, leading 3-1.
The two players first locked horns in the first round of the 2018 Miami Open with the Japanese winning 6-3, 6-2. Osaka then beat Serena Williams 6-2, 6-4 in the 2018 US Open final to win her maiden Grand Slam singles title.
Williams beat Osaka for the first time in the quarter-finals of the 2019 Rogers Cup. However, the Japanese won their fourth meeting, which came in the semi-finals of the 2021 Australian Open. Osaka won 6-3, 6-4 to reach the final where she beat Jennifer Brady to win her fourth Grand Slam singles title.
#3 Bianca Andreescu: 2-0
Bianca Andreescu has faced Serena Williams in two finals, winning both of them. The first encounter between the two came in the title clash of the 2019 Rogers Cup. Andreescu led 3-1 in the opening set before Williams was forced to retire due to back spasms.
The two then locked horns in the US Open final a few weeks later. This time, the entirety of the match was played and Andreescu won 6-3, 7-5 to win her maiden Grand Slam title. The Canadian thus became the first player born in the 2000s to win a Major.
#4 Sybille Bammer: 2-0
Austria's Sybille Bammer did not have the most illustrious of careers in tennis but she retired with a feat that was quite elusive – having a perfect head-to-head record against Serena Williams.
The first meeting between the two players came in the quarter-finals of the 2007 Moorilla Hobart International. Serena won the opening set 6-3 but Bammer bounced back to win the next two sets and reach the semi-finals of the tournament, where she would lose to Vasilisa Bardina.
The Austrian met Williams for the second time in the third round of the Western & Southern Financial Group Women's Open. This time, she won 7-5, 6-4 to reach the quarter-finals, where she was thrashed 0-6, 3-6 by eventual champion Jelena Jankovic.
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