![Serena Williams matches with daughter in custom figure skating-inspired Nike dress at US Open - Good Morning America Serena Williams matches with daughter in custom figure skating-inspired Nike dress at US Open - Good Morning America](https://s.abcnews.com/images/Sports/serena-williams-daring-tennis-fashions-us-open-1999-06-gty-llr-220829_1661819257982_hpEmbed_8x11_608.jpg)
Serena Williams matches with daughter in custom figure skating-inspired Nike dress at US Open - Good Morning America
![Serena vs. Hingis: When teenage Grand Slam finals were the norm - Official Site of the 2023 US Open Tennis Championships - A USTA Event Serena vs. Hingis: When teenage Grand Slam finals were the norm - Official Site of the 2023 US Open Tennis Championships - A USTA Event](https://photo-assets.usopen.org/images/pics/large/f_Serena-1999_50th.jpg)
Serena vs. Hingis: When teenage Grand Slam finals were the norm - Official Site of the 2023 US Open Tennis Championships - A USTA Event
![SERENA WILLIAMS at 1999 US open National Tennis Center Flushing Meadows New York.k16448ar. © Andrea Renault/Globe Photos/ZUMA Wire/ZUMA Wire/Alamy Live News Stock Photo - Alamy SERENA WILLIAMS at 1999 US open National Tennis Center Flushing Meadows New York.k16448ar. © Andrea Renault/Globe Photos/ZUMA Wire/ZUMA Wire/Alamy Live News Stock Photo - Alamy](https://c8.alamy.com/comp/F0PDY0/serena-williams-at-1999-us-open-national-tennis-center-flushing-meadows-F0PDY0.jpg)
SERENA WILLIAMS at 1999 US open National Tennis Center Flushing Meadows New York.k16448ar. © Andrea Renault/Globe Photos/ZUMA Wire/ZUMA Wire/Alamy Live News Stock Photo - Alamy
![U.S. Open Preview: Serena Williams's Swan Song, Her Doubles Dream Team, And… Another Surprise Winner? | Vogue U.S. Open Preview: Serena Williams's Swan Song, Her Doubles Dream Team, And… Another Surprise Winner? | Vogue](https://assets.vogue.com/photos/630b93d121841725dc495d9b/master/w_2560%2Cc_limit/GettyImages-72480880.jpg)
U.S. Open Preview: Serena Williams's Swan Song, Her Doubles Dream Team, And… Another Surprise Winner? | Vogue
![Serena Williams, Venus Williams walk off court in likely last doubles match together - Good Morning America Serena Williams, Venus Williams walk off court in likely last doubles match together - Good Morning America](https://s.abcnews.com/images/US/venus-serena-williams-doubles-usopen-1999--02-gty-llr-220901_1662083891869_hpEmbed_19x13_992.jpg)
Serena Williams, Venus Williams walk off court in likely last doubles match together - Good Morning America
![That Championship Season: Little sister Serena strikes first, 1999 - Official Site of the 2023 US Open Tennis Championships - A USTA Event That Championship Season: Little sister Serena strikes first, 1999 - Official Site of the 2023 US Open Tennis Championships - A USTA Event](https://photo-assets.usopen.org/images/pics/large/f_Serena1999_2.jpg)
That Championship Season: Little sister Serena strikes first, 1999 - Official Site of the 2023 US Open Tennis Championships - A USTA Event
![25 years of Arthur Ashe Stadium: Serena Williams announces herself in first Grand Slam win, 1999 - Official Site of the 2023 US Open Tennis Championships - A USTA Event 25 years of Arthur Ashe Stadium: Serena Williams announces herself in first Grand Slam win, 1999 - Official Site of the 2023 US Open Tennis Championships - A USTA Event](https://photo-assets.usopen.org/images/pics/large/f_GettyImages-52841981.jpg)
25 years of Arthur Ashe Stadium: Serena Williams announces herself in first Grand Slam win, 1999 - Official Site of the 2023 US Open Tennis Championships - A USTA Event
![Serena Williams (USA) with Martina Hingis (SWI) wins her first Grand Slam at the 1999 US Open Tennis Championship Stock Photo - Alamy Serena Williams (USA) with Martina Hingis (SWI) wins her first Grand Slam at the 1999 US Open Tennis Championship Stock Photo - Alamy](https://c8.alamy.com/comp/2G5GTR3/serena-williams-usa-with-martina-hingis-swi-wins-her-first-grand-slam-at-the-1999-us-open-tennis-championship-2G5GTR3.jpg)
Serena Williams (USA) with Martina Hingis (SWI) wins her first Grand Slam at the 1999 US Open Tennis Championship Stock Photo - Alamy
![With her galvanizing win at the U.S. Open, Serena Williams proved Dad right but may have created family tension - Sports Illustrated Vault | SI.com With her galvanizing win at the U.S. Open, Serena Williams proved Dad right but may have created family tension - Sports Illustrated Vault | SI.com](https://vault.si.com/.image/t_share/MTY5MTE4NjEzMTg4NzgxNTMx/serena-uso-action-99jpg.jpg)
With her galvanizing win at the U.S. Open, Serena Williams proved Dad right but may have created family tension - Sports Illustrated Vault | SI.com
![US Open Moments: Sept. 4, 1999 - Official Site of the 2023 US Open Tennis Championships - A USTA Event US Open Moments: Sept. 4, 1999 - Official Site of the 2023 US Open Tennis Championships - A USTA Event](https://photo-assets.usopen.org/images/pics/large/f_Serena.1999USO.jpg)
US Open Moments: Sept. 4, 1999 - Official Site of the 2023 US Open Tennis Championships - A USTA Event
![MG Burton on Twitter: "#ForebearerFridays On Sept. 11, 1999, Serena Williams, age 17, wins the U.S. Open, her first major tennis championship. She has who won more Grand Slam singles titles (23) MG Burton on Twitter: "#ForebearerFridays On Sept. 11, 1999, Serena Williams, age 17, wins the U.S. Open, her first major tennis championship. She has who won more Grand Slam singles titles (23)](https://pbs.twimg.com/media/EhpWprYWAAInbSX.jpg)