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A 16-year-old Serena competed in a tennis "Battle of the Sexes", along with her sister [[Venus Williams]], against [[Karsten Braasch]] at the 1998 Australian Open.<ref>[https://web.archive.org/web/20130413074213/http://www.ontennis.com/news/serena-williams-still-savouring-andy-roddick-%26%23039%3Bwin%26%23039%3B-16-years "Serena Williams still savouring Andy Roddick 'win' 16 years on"], OnTennis.com, posted January 22, 2009</ref> At the time Braasch was 203rd in the ATP rankings. The Williams sisters had claimed they could beat any man outside the top 200, and accepted his challenge. Braasch beat both Williams sisters, playing a single set against each. The score vs Serena was 6–1 and vs Venus 6–2.<ref>Steve Wilstein (January 27, 1998), [http://www.apnewsarchive.com/1998/Sister-Act-Falls-in-Battle-of-Sexes/id-5dc73280424bc3fe43f41dfaeb943f43 "Sister Act Falls In Battle Of Sexes"]. Associated Press. Retrieved April 29, 2017.</ref> Braasch said afterward, "500 and above, no chance." The sisters later tweaked the number to beating men outside the top 350.<ref>{{cite web|url=http://www.dispatch.co.za/1998/01/28/sport/WILLIAMS.HTM |title=Welcome to Dispatch Online |website=Daily Dispatch |date=November 12, 2010 |accessdate=March 20, 2011 |url-status=dead |archiveurl=https://web.archive.org/web/20090428044804/http://www.dispatch.co.za/1998/01/28/sport/WILLIAMS.HTM |archivedate=April 28, 2009 |df=}}</ref>
====Different Strokes: Serena, Venus, and the Unfinished Black Tennis Revolution====
{{Main|Different_Strokes_(tennis)#2002:_Lindsay_Davenport_vs._Serena_Williams|11=Different Strokes (tennis)}}
Serena was the No. 1 seed, along with her sister [[Venus Williams]], and she was against [[Ameile Mauresmo]] at the 2002 U.S. Open semifinals. In Venus's semifinal, she served for the match at 5-4 in the third set. When she lost the first three points to give to Mauresmo triple break point. Venus showed her mental toughness and won the match 6-3, 5-7, 6-4. In Serena's semifinal, her unforced errors and double faults were often cheered by a crowd that responded to Davenport's unforced errors. Still, Serena drew upon her mental strength and prevailed, 6-3, 7-5.
===1999–2001: Becoming a top-10 player===
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