![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
![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
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Serena Williams (USA) wins her first Grand Slam at the 1999 US Open Tennis Championship Stock Photo - Alamy
![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_GettyImages-72283925.jpg)
Serena vs. Hingis: When teenage Grand Slam finals were the norm - Official Site of the 2023 US Open Tennis Championships - A USTA Event
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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
![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
![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
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U.S. Open Preview: Serena Williams's Swan Song, Her Doubles Dream Team, And… Another Surprise Winner? | Vogue
![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 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
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