Watch now

In photos: 16 rivals that defined Serena's iconic career

Venus may have been Serena's best rival, but plenty of other elite athletes challenged the 23-time Grand Slam champion over nearly three decades on tour. Relive the best moments from Serena's greatest rivalries.

By David Kane
Tennis Channel Live: S. Williams vs M. Sharapova; 2019 US Open 1R2:16
WATCH: Serena played her last match against Maria Sharapova at the 2019 US Open.
29 May 1998: Serena Williams of the USA plays a backhand during the 1998 French Open played at Roland Garros, Paris, France. \ Mandatory Credit: Clive Brunskill /Allsport
© Getty Images
7 Sep 2001: Serena Williams of USA and Martina Hingis of Switzerland pose by the net before the semifinals of the US Open at USTA National Tennis Center in Flushing, New York. Williams beat Hingis 6-3, 6-2. DIGITAL IMAGE. Mandatory Credit: Ezra Shaw/ALLSPORT
© Getty Images
MELBOURNE - JANUARY 23: Serena Williams of the USA (left) embraces Kim Clijsters of Belgium after winning their match in three sets during the Australian Open Tennis Championships at Melbourne Park in Melbourne, Australia on January 23, 2003. (Photo by Clive Brunskill/Getty Images).
© Getty Images
ROME - MAY 15: Jennifer Capriati of USA and Serena Williams of USA embrace after Capriati'svictory in the Women's Telecom Italia Tennis Masters at the Foro Italico on May 15, 2004 in Rome. (Photo by Mike Hewitt/Getty Images)
© 2004 Getty Images
MELBOURNE, AUSTRALIA - JANUARY 27: Serena Williams of the USA celebrates match point against Maria Sharapova of Russia during day eleven of the Australian Open Grand Slam at Melbourne Park January 27, 2005 in Melbourne, Australia. Williams defeated Sharapova 2-6, 7-5, 8-6. (Photo by Nick Laham/Getty Images)
© 2005 Getty Images
MELBOURNE, Australia: Winner Serena Williams (L) of the US poses with runner-up and compatriot Lindsay Davenport while holding their respective awards following the women's singles final at the 2005 Australian Open tennis tournament in Melbourne, 29 January 2005. Williams won the match 2-6, 6-3, 6-0 to take the title. AFP PHOTO/WILLIAM WEST (Photo credit should read WILLIAM WEST/AFP via Getty Images)
© AFP via Getty Images
WIMBLEDON, ENGLAND - JULY 02: Elena Dementieva of Russia plays a forehand during the women's singles semi final match against Serena Williams of USA on Day Ten of the Wimbledon Lawn Tennis Championships at the All England Lawn Tennis and Croquet Club on July 2, 2009 in London, England. (Photo by Julian Finney/Getty Images)
© 2009 Getty Images
Winner Serena Williams of the US (R) smiles as she poses with Justine Henin of Belgium (L) before receiving their trophies at the awards ceremony following their women's final match on day 13 of the Australian Open tennis tournament in Melbourne on January 30, 2010. Williams won 6-4, 3-6, 6-2 to take the title. AFP PHOTO / GREG WOOD (Photo credit should read GREG WOOD/AFP via Getty Images)
© AFP via Getty Images
MELBOURNE, AUSTRALIA - JANUARY 17: Serena Williams of the United States of America and Samantha Stosur of Australia and of the Red Team share a laugh during the "Hit For Haiti" charity exhibition match ahead of the 2010 Australian Open at Melbourne Park on January 17, 2010 in Melbourne, Australia. (Photo by Mark Dadswell/Getty Images)
© 2010 Getty Images
Serena Williams of the US (R) celebrates with the trophy after defeating Jelena Jankovic (L) of Serbia after their women's singles finals match at the China Open tennis tournament in Beijing on October 6, 2013. Williams went on to win 6-2, 6-2. AFP PHOTO / Mark RALSTON (Photo credit should read MARK RALSTON/AFP via Getty Images)
© AFP via Getty Images
US player Serena Williams (L) holds the winner's trophy, the Venus Rosewater Dish, after her women's singles final victory over Spain's Garbine Muguruza (R) who holds the runners up shield on day twelve of the 2015 Wimbledon Championships at The All England Tennis Club in Wimbledon, southwest London, on July 11, 2015. Williams won 6-4, 6-4. RESTRICTED TO EDITORIAL USE -- AFP PHOTO / POOL / SEAN DEMPSEY (Photo by SEAN DEMPSEY / POOL / AFP) (Photo by SEAN DEMPSEY/POOL/AFP via Getty Images)
© POOL/AFP via Getty Images
CINCINNATI, OH - AUGUST 23: Serena Williams (R) shakes hands with Simona Halep of Romania after defeating her during the finals of the Western & Southern Open at the Linder Family Tennis Center on August 23, 2015 in Cincinnati, Ohio. (Photo by Rob Carr/Getty Images)
© 2015 Getty Images
Angelique Kerber of Germany (R) is congratulated during the awards ceremony by Serena Williams of the US (L) after Kerber's victory in their women's singles final match on day 13 of the 2016 Australian Open tennis tournament in Melbourne on January 30, 2016. AFP PHOTO / PAUL CROCK -- IMAGE RESTRICTED TO EDITORIAL USE - STRICTLY NO COMMERCIAL USE / AFP / PAUL CROCK (Photo credit should read PAUL CROCK/AFP via Getty Images)
© AFP via Getty Images
INDIAN WELLS, CA - MARCH 20: Victoria Azarenka of Belarus laughs with the winners trophy as Serena Williams of USA pulls a face after the final during day fourteen of the BNP Paribas Open at Indian Wells Tennis Garden on March 20, 2016 in Indian Wells, California. (Photo by Julian Finney/Getty Images)
© 2016 Getty Images
US Serena Williams shakes hands with Czech Republic's Karolina Pliskova after defeating her during their Women's Singles Quarter-Finals match a the 2018 US Open at the USTA Billie Jean King National Tennis Center in New York on September 4, 2018. - Six-time champion Serena Williams overpowered Karolina Pliskova 6-4, 6-3 on Tuesday to reach the semi-finals of the US Open. (Photo by EDUARDO MUNOZ ALVAREZ / AFP) (Photo credit should read EDUARDO MUNOZ ALVAREZ/AFP via Getty Images)
© AFP via Getty Images
Serena Williams of the US and Japan's Naomi Osaka (L) pose for pictures before their women's singles match at the 'A Day at the Drive' exhibition tennis tournament in Adelaide on January 29, 2021. (Photo by Brenton Edwards / AFP) (Photo by BRENTON EDWARDS/AFP via Getty Images)
© AFP via Getty Images