5 players who have won the most matches against Serena Williams ft. Venus Williams and Jennifer Capriati

Serena Williamssaddened the tennis world by announcing that she would retire after the upcoming US Open. Williams strode like a colossus in her heyday, overcoming the toughest opponents and breaking records along the way.

The tennis legend has an impeccable array of statistics to her name, and there are not many players who have managed to defeat her on multiple occasions.

Let's take a look at five players who have beaten the American star the most number of times.

---

#5 Victoria Azarenka - Defeated Serena Williams 5 times

The Belarusian has an impressive record against Serena Williams, having beaten the 23-time Grand Slam champion five times.

Although she lost to Williams on 18 occasions, Azarenka did manage to get the better of her more illustrious opponent in comprehensive fashion. At the 2009 Miami Open final, Azarenka emerged victorious with a 6-3, 6-1 scoreline.

The former World No. 1 had to fight harder to beat her rival in the finals at Doha in 2013 where she edged past Williams in the opening set tiebreak before winning 7-6(6), 2–6, 6–3.

Azarenka defeated Williams yet again in the finals of the Cincinnati Open the same year, coming through thanks to winning a close tiebreak in decider 2–6, 6–2, 7–6(8–6).

The two-time Australian Open champion had a penchant for beating Williams in the big finals as she prevailed for a fourth time at Indian Wells in 2016 in straight sets 6–4, 6–4.

Her fifth win against the American came in the semifinals of the 2020 US Open, with Williams chasing an elusive 24th Grand Slam title in a quest to draw level with Margaret Court's record.

---

#4 Justine Henin - Defeated Serena Williams 6 times

Justine Henin developed an epic rivalry with Serena Williams, being one of the few players to consistently challenge the American. While Williams led the overall head-to-head 8-6, Henin led 4-3 in Grand Slam events.

After a couple of losses against the American in 2001, Henin got revenge in the final of the German Open a year later, winning 6–2, 1–6, 7–6(5).

The see-saw battle continued, with Serena Williams winning the next two encounters before the seven-time Grand Slam champion took just over an hour to overcome her opponent 6–3, 6–4 in the final of the 2003 Charleston Open.

Henin also overcame her rival in the semifinals of the French Open in the same year 6–2, 4–6, 7–5. After a four-year hiatus, the rivalry resumed with Serena Williams reigning supreme in the final of the Miami Open before Henin registered a hat-trick of wins in three consecutive Grand Slam quarterfinals, all in the same year as well.

A 6–4, 6–3 win at Roland Garros was followed by a 6–4, 3–6, 6–3 victory in the 2007 Wimbledon quarterfinals. The Belgian was unrelenting and prevailed in the quarterfinals of the US Open the same year with a 7–6(3), 6–1 scoreline.

Her win at the US Open was her last over the American and Williams won the last of their two encounters before Henin retired in 2011.

---

#3 Martina Hingis - Defeated Serena Williams 6 times

Martina Hingis had the upper hand in the initial stages of their rivalry against an up-and-coming Serena Williams back in 1998, with a couple of wins in the quarterfinals of the Miami Open and the LA Women's Tennis Championships.

Williams went down fighting 6–3, 1–6, 7–6(4) in Miami while Hingis had an easier outing in Los Angeles, winning 6-4, 6-1.

The American got her revenge in the semifinals of the Miami Open the following year while Hingis prevailed soon after in the quarterfinals of the Italian Open 6-2, 6-2.

Serena Williams retired midway through the Canadian Open final in 2000 but lost to the Swiss player in the 2001 Sydney International 6-4, 7-5 and at the quarterfinals of the Australian Open immediately after. Their encounter in Melbourne was one of their most gruelling clashes and Hingis won 6–2, 3–6, 8–6.

As Williams gradually emerged to become a more complete player, Hingis failed to get past her in three of their final meetings.

---

#2 Jennifer Capriati - Defeated Serena Williams 7 times

The three-time Grand Slam champion first beat Serena Williams at the 2000 Miami Open and won their next match in the quarterfinals of the 2001 Wimbledon Championships 6-7 (4), 7-5, 6-3.

After a string of losses against Williams, Capriati beat Williams in the semifinals of the 2004 Italian Open after a gap of three years.

Capriati got past her rival one last time in a controversial US Open quarterfinal in 2004. The a contest that was marred by erroneous calls by the line and chair umpire, with the score that read 2-6, 6-4, 6-4 in Capriati's favor.

In all, Capriati managed to beat Williams seven times between 1999 and 2004 while going down 10 times against her fellow American rival.

#1 Venus Williams - Defeated Serena Williams 12 times

No player has defeated Serena Williams more times than sister Venus Williams.

The legendary duo dominated the tour while playing in the doubles events but developed an epic on-court rivalry that began in the second round of the 1998 Australian Open, with Venus winning 7-6(4), 6-1.

Venus also won the first-ever WTA tour singles final between the two at the 1999 Lipton International Players' Championships.

Venus emerged victorious on the Grand Slam stage as well, getting past Serena in the semifinals of the 2000 Wimbledon Championships.

The duo competed against each other in a Grand Slam final at the 2001 US Open, with Venus overcoming her sister with ease 6-2, 6-4.

Serena tilted the scales in 2002, winning all four contests that the Williams sisters were part of that season.

Venus and Serena played each other in two Grand Slam finals in 2003, with the younger of the two sisters emerging triumphant on both occasions before Venus ended up on the winning side in the 2005 NASDAQ-100 Open 6–1, 7–6(8).

A classic Wimbledon final in 2008 witnessed defending champion Venus Williams defeating Serena 7-5, 6-4.

After beating Venus five times in a row, Serena failed to get past her sister in the semifinals of the 2014 Rogers Cup, losing 6–7(2), 6–2, 6–3.

While Serena won their last Grand Slam final competing against each other at the 2017 Australian Open, the third round of the BNP Paribas Open in 2018 brought the two sisters face-to-face on the court once more, with Venus winning 6–3, 6–4.