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===1995–1998: Professional debut=== {{Main|Serena Williams's early career}} Williams's parents initially wanted their daughter to wait until she was 16 to participate in professional tournaments.<ref name=tradition>{{cite news |last=Finn |first=Robin |title=Tennis; A Family Tradition At Age 14 |work=The New York Times |date=31 October 1995 |url=https://www.nytimes.com/1995/10/31/sports/tennis-a-family-tradition-at-age-14.html |access-date=13 July 2019 |archive-date=6 April 2023 |archive-url=https://web.archive.org/web/20230406050124/https://www.nytimes.com/1995/10/31/sports/tennis-a-family-tradition-at-age-14.html |url-status=live }}</ref> In 1995, just after turning 14, Williams planned to make her professional debut as a [[Wild card (sports)#Professional tennis|wild-card]] entry in the [[Bank of the West Classic]] in [[Oakland, California|Oakland]], California, but was denied due to age-eligibility restrictions.<ref name=Finn>{{cite news |last=Finn |first=Robin |title=Tennis; Teen-Ager, Fighting To Turn Pro At 14, Puts Off Lawsuit For Now |work=The New York Times |date=6 October 1995 |url=https://www.nytimes.com/1995/10/06/sports/tennis-teen-ager-fighting-to-turn-pro-at-14-puts-off-lawsuit-for-now.html |access-date=13 July 2019 |archive-date=6 April 2023 |archive-url=https://web.archive.org/web/20230406035639/https://www.nytimes.com/1995/10/06/sports/tennis-teen-ager-fighting-to-turn-pro-at-14-puts-off-lawsuit-for-now.html |url-status=live }}</ref> She subsequently filed an antitrust lawsuit against the WTA, but withdrew it at her parents' request.<ref name=Finn/> Her first professional event was in October 1995 at the [[Bell Challenge]] in Quebec,<ref name=tradition/><ref>{{cite news |title=Tennis Muster Stuns Sampras Indoors In Germany |work=The New York Times |date=29 October 1995 |url=https://www.nytimes.com/1995/10/29/sports/results-plus-859495.html |access-date=13 July 2019 |archive-date=6 April 2023 |archive-url=https://web.archive.org/web/20230406195430/https://www.nytimes.com/1995/10/29/sports/results-plus-859495.html | url-status=live }}</ref> where she used a wild-card entry to circumvent age-eligibility rules.<ref name=tradition/> She lost in the first qualifying round to 18-year-old American [[Annie Miller (tennis)|Annie Miller]].<ref>{{cite web |url=https://www.espn.com/espnw/news-commentary/story/_/id/12167370/what-ever-happened-first-person-beat-serena-williams |title=Whatever happened to the first person to beat Serena Williams? |work=ESPN |date=14 January 2015 |access-date=22 December 2023}}</ref> After not playing in 1996, Williams won her first main-draw match at the [[Ameritech Cup Chicago]] in November 1997.<ref name=tennispal/><ref name=youngerwilliams>{{cite news |title=Tennis: Roundup; Younger Williams Wins In Chicago |work=The New York Times |date=4 November 1997 |url=https://www.nytimes.com/1997/11/04/sports/tennis-roundup-younger-williams-wins-in-chicago.html |access-date=13 July 2019 |archive-date=6 April 2023 |archive-url=https://web.archive.org/web/20230406114507/https://www.nytimes.com/1997/11/04/sports/tennis-roundup-younger-williams-wins-in-chicago.html |url-status=live }}</ref> Ranked No.304, she upset No.7 [[Mary Pierce]] and No.4 [[Monica Seles]],<ref>{{cite news |title=Serena Williams Upsets Pierce |work=The New York Times |date=7 November 1997 |url=https://www.nytimes.com/1997/11/07/sports/tennis-roundup.html |access-date=13 July 2019 |archive-date=6 April 2023 | archive-url=https://web.archive.org/web/20230406102402/https://www.nytimes.com/1997/11/07/sports/tennis-roundup.html |url-status=live }}</ref> recording her first career wins over top{{nbsp}}10 players and becoming the lowest-ranked player in the Open Era to defeat two top-10 opponents in one tournament.<ref name=Card>{{cite web |url=https://www.espn.com/sports/tennis/playerCard?player=serena |title=ESPN.com: SWILLIAMS PlayerCard |work=ESPN |access-date=22 December 2023}}</ref> She ultimately lost in the semifinals to No.5 [[Lindsay Davenport]].<ref>{{cite news |agency=Associated Press |title=Tennis: Roundup – Ameritech Open; Serena Williams Loses In Semi |work=The New York Times |date=9 November 1997 |url=https://www.nytimes.com/1997/11/09/sports/tennis-roundup-ameritech-open-serena-williams-loses-in-semi.html |access-date=13 July 2019 |archive-date=July 14, 2019 |archive-url=https://web.archive.org/web/20190714051231/https://www.nytimes.com/1997/11/09/sports/tennis-roundup-ameritech-open-serena-williams-loses-in-semi.html |url-status=live }}</ref> Her run in Chicago propelled Williams into the Top 100 for the first time in her career, and she finished 1997 ranked No.99 in the world.<ref name=sportytell/><ref name=Fed>{{cite web |url=https://www.usta.com/en/home/pro/pro-media---news/remembering-serena-williams--fed-cup-debut-in-1999.html |title=Remembering Serena's 1999 Fed Cup debut |website=www.usta.com |date=31 January 2020 |access-date=22 December 2023}}</ref> At the 1998 [[Medibank International Sydney|Sydney International]], Williams defeated No.3 Davenport in the quarterfinals, before losing to [[Arantxa Sánchez Vicario]] in the semifinals.<ref>{{cite news |last=Stevenson |first=Samantha |title=Tennis; Williams Sisters Won't Meet in the Final |work=The New York Times |date=16 January 1998 |url=https://www.nytimes.com/1998/01/16/sports/tennis-williams-sisters-won-t-meet-in-the-final.html |access-date=13 July 2019 |archive-date=6 April 2023 |archive-url=https://web.archive.org/web/20230406210728/https://www.nytimes.com/1998/01/16/sports/tennis-williams-sisters-won-t-meet-in-the-final.html |url-status=live }}</ref> Williams's first main draw of a Grand Slam tournament was at the [[1998 Australian Open|Australian Open]], where she defeated sixth-seeded [[Irina Spîrlea]] in the first round, before losing to Venus in the second round in the sisters' first professional face-off.<ref name=Card/><ref name=Irina>{{cite news |last=Finn |first=Robin |title=Tennis; In Williams vs. Williams, Big Sister Moves Ahead |work=The New York Times |date=January 21, 1998 |url=https://www.nytimes.com/1998/01/21/sports/tennis-in-williams-vs-williams-big-sister-moves-ahead.html |access-date=July 13, 2019 |archive-date=April 6, 2023 |archive-url=https://web.archive.org/web/20230406035637/https://www.nytimes.com/1998/01/21/sports/tennis-in-williams-vs-williams-big-sister-moves-ahead.html |url-status=live }}</ref> She reached six other quarterfinals during the year, but lost all of them, including her first match against No.1-ranked [[Martina Hingis]].<ref>{{cite web |url=https://www.nytimes.com/1998/03/25/sports/tennis-hingis-escapes-one-williams-and-will-face-the-other.html |title=Hingis Escapes One Williams, and Will Face the Other |website=www.nytimes.com |date=25 March 1998 |access-date=22 December 2023}}</ref><ref name=Looney>{{cite news |first=Douglas S. |last=Looney |title=Venus Rising |work=[[The Christian Science Monitor]] |date=May 22, 1998 |url=https://www.csmonitor.com/1998/0522/052298.feat.feat.2.html |access-date=July 14, 2019 |archive-date=April 5, 2023 |archive-url=https://web.archive.org/web/20230405074148/https://www.csmonitor.com/1998/0522/052298.feat.feat.2.html |url-status=live }}</ref> She lost in the fourth round of the [[1998 French Open – Women's singles|French Open]] to Vicario,<ref>{{cite news |last=Finn |first=Robin |title=Tennis; Emotions Hit the Heights In Bitter Day on the Clay |work=The New York Times |date=June 1, 1998 |url=https://www.nytimes.com/1998/06/01/sports/tennis-emotions-hit-the-heights-in-bitter-day-on-the-clay.html |access-date=July 14, 2019 |archive-date=April 6, 2023 |archive-url=https://web.archive.org/web/20230406131033/https://www.nytimes.com/1998/06/01/sports/tennis-emotions-hit-the-heights-in-bitter-day-on-the-clay.html |url-status=live }}</ref> and in the third round of the [[1998 US Open – Women's singles|US Open]] to Spîrlea.<ref>{{cite news |last=Clarey |first=Christopher |title=Tennis: U.S. Open; One Year Later, Spirlea Defeats a Williams Sister |work=The New York Times |date=September 5, 1998 |url=https://www.nytimes.com/1998/09/05/sports/tennis-us-open-one-year-later-spirlea-defeats-a-williams-sister.html |access-date=July 14, 2019 |archive-date=April 5, 2023 |archive-url=https://web.archive.org/web/20230405211850/https://www.nytimes.com/1998/09/05/sports/tennis-us-open-one-year-later-spirlea-defeats-a-williams-sister.html |url-status=live }}</ref> She withdrew from [[1998 Wimbledon Championships – Women's singles|Wimbledon]] two games into a match after straining a calf muscle.<ref>{{cite news |last=Finn |first=Robin |title=Tennis; Serena Williams Is Out; Henman Uplifts Locals |work=The New York Times |date=June 30, 1998 |url=https://www.nytimes.com/1998/06/30/sports/tennis-serena-williams-is-out-henman-uplifts-locals.html |access-date=July 14, 2019 |archive-date=April 6, 2023 |archive-url=https://web.archive.org/web/20230406035637/https://www.nytimes.com/1998/06/30/sports/tennis-serena-williams-is-out-henman-uplifts-locals.html |url-status=live }}</ref> After losing the [[1998 French Open – Mixed doubles|French Open]] mixed doubles final to Venus and [[Justin Gimelstob]], Williams won the mixed doubles titles at [[1998 Wimbledon Championships – Mixed doubles|Wimbledon]] and the [[1998 US Open – Mixed doubles|US Open]] with [[Max Mirnyi]].<ref>{{cite web |url=https://www.tennis.com/news/articles/on-this-day-serena-williams-wins-wimbledon-mixed-doubles-title-1998 |title=On this day 25 years ago: 16-year-old Serena Williams wins Wimbledon mixed doubles title |website=www.tennis.com |date=5 July 2023 |accessdate=22 December 2023}}</ref> Williams won her first professional title in non-mixed doubles at the [[U.S. National Indoor Championships]] in Oklahoma City with Venus, which made them the third pair of sisters to win a WTA title.<ref>{{cite web |url=https://www.tennis.com/baseline/articles/on-this-day-1998-venus-williams-wins-first-wta-title-in-oklahoma-city-serena |title=25 Years Ago: Venus Williams' titanic day in Oklahoma City |website=www.tennis.com |date=1 March 2023 |accessdate=22 December 2023}}</ref> Williams finished the year ranked No.20 in singles, the fastest achievement of that milestone in women's history.<ref name="rankingshistory">{{cite web |title=Serena Williams ranking history at the WTA |url=https://www.wtatennis.com/players/230234/serena-williams#rankingshistory |accessdate=18 December 2023 |website=www.wtatennis.com}}</ref><ref name=memorable>{{cite web |url=https://www.wtatennis.com/news/2772210/1995-1999-the-beginning-of-a-memorable-career |title=1995–1999: The beginning of a memorable care |website=www.wtatennis.com |date=31 August 2022 |access-date=22 December 2023}}</ref>
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