# 1999 Serena Williams tennis season

The Serena Williams 1999 season was her breakthrough season, winning her first career title at the Open Gaz de France and winning her first slam at the US Open.

## Year summary
### Early hard court season

At the Australian Open, Williams lost in the third round to Sandrine Testud despite holding two match points. After two losses in tight three-setters in Australia, at the hands of Testud in Melbourne and Steffi Graf in Sydney, Williams won her first professional singles title when she defeated Amélie Mauresmo in the final of the Open Gaz de France in Paris, thus becoming the 13th unseeded player to win a Tier II or higher event since 1980. With Venus also winning the IGA Superthrift Classic in Memphis, Tennessee, that day, the pair became the first sisters to win professional tournaments in the same week.
In March of that year, at the Evert Cup in California, Williams won her first WTA 1000 event, defeating a 29-year-old Steffi Graf in the final, thus ending Graf's completed finals winning streak at 20, which dated back to 1995. Soon afterward at the Miami Masters, Williams had her 16-match winning streak ended by her sister in the first all-sister singles final in WTA history and the first all-sister women's final in 115 years, with the only other such final taking place at Wimbledon in 1884, when Maud Watson beat her older sister, Lilian, to become Wimbledon's first female champion. This was the best winning streak that includes a player's first title since Steffi Graf's 23-match streak in 1986. Williams then made her top-10 debut, at No. 9.

### Clay court season

Williams lost in the quarterfinals of the Italian Open and the German Open. At the French Open, Williams lost in the third round to Mary Joe Fernández, but in the doubles event, she and Venus did not drop a single set en route to the final, where they defeated the pair of Martina Hingis and Anna Kournikova, who were the self-proclaimed "Spice Girls" of tennis, having dropped just a single set on their route to the Australian Open doubles title. It was the first major title for the Williams sisters and would be their first step towards completing the career Golden Slam in doubles.
Williams then missed Wimbledon because of injury. When she returned to the tour two months later, Williams made her Fed Cup debut. After a two-and-a-half-hour rain delay and with Monica Seles unavailable, the USTA and U.S. captain Billie Jean King turned to her other rookie, 17-year-old Serena, to try to close out the tie. Williams did just that, toppling Rita Grande, 6-1, 6-1, in 50 minutes, thus sending the U.S. back to the final for the first time since 1996. In doing so at 17 years and nine months old, she became the sixth youngest player in US Fed Cup history to win a match. The Williams sisters, who were traveling internationally without their parents for the first time in their careers, then teamed up to win the dead doubles rubber against Tathiana Garbin and Adriana Serra Zanetti, to cap a perfect debut. She then won her third title at the JPMorgan Chase Open in Los Angeles, beating Julie Halard-Decugis in the final. This moved her ranking back into the Top 10 at No. 9, tying her career high.

### Late hard court season

At the US Open, Williams defeated Grand Slam champions Kim Clijsters, Conchita Martínez, Monica Seles, and defending champion Lindsay Davenport in consecutive matches to reach the final, where she faced the world No. 1, the 18-year-old Martina Hingis, who had defeated her sister in the semifinals and also in the 1997 US Open final. She finished the job that her sister could not by beating Hingis 6–3, 7–6$^{(7–4)}$ to capture her first US Open title at age 17 in only her second year as a pro; she won despite making 57 unforced errors, 33 more than Hingis. In doing so, she became the lowest seed to win the US Open in the Open era, the sixth American woman in the Open Era to win a Major, and only the second African-American woman, after Althea Gibson in 1958, to win a Grand Slam singles tournament.
In the doubles event, the Williams sisters defeated Chanda Rubin and Sandrine Testud in the final, 4–6, 6–1, 6–4 to win the women's doubles title. It was the second doubles major title for the Williams sisters, and their second step towards completing the career Golden Slam in doubles. Serena thus became the fifth woman in the Open Era to win both the singles and doubles event of a major, while she and Venus became the first sisters to win a US Open doubles championship in 101 years, since Juliette and Kathleen Atkinson accomplished it in 1897 and 1898. In total, the Williams girls earned $1.29 million for their two-week US Open travel, $915,000 of it reeled in by Serena.
To complete her 1999 season, Williams teamed up with Venus to win a doubles match in the Fed Cup final to help Team USA win the 1999 Fed Cup title against Russia at the Taube Family Tennis Stadium in Stanford, Calif. Williams ended the year ranked in a career-high world No. 4 in just her second full year on the main tour.

## All matches
### Singles matches

| Tournament | Match | Round | Opponent | Rank | Result | Score |
| Sydney International Sydney, Australia Tier II Hard, outdoor 11–17 January 1999 | 56 | 1R | Inés Gorrochategui | #208 | Win | 6–4, 6–2 |
| Sydney International Sydney, Australia Tier II Hard, outdoor 11–17 January 1999 | 57 | 2R | Steffi Graf | #10 | Loss | 2–6, 6–3, 5–7 |
| Australian Open Melbourne, Australia Grand Slam Hard, outdoor 18–31 January 1999 | 58 | 1R | Raluca Sandu | #99 | Win | 6–2, 6–3 |
| Australian Open Melbourne, Australia Grand Slam Hard, outdoor 18–31 January 1999 | 59 | 2R | Magüi Serna | #22 | Win | 6–1, 6–3 |
| Australian Open Melbourne, Australia Grand Slam Hard, outdoor 18–31 January 1999 | 60 | 3R | Sandrine Testud | #15 | Loss | 2–6, 6–2, 7–9 |
| Open Gaz de France Paris, France Tier II Hard, outdoor 22–28 February 1999 | 61 | 1R | Åsa Svensson | #94 | Win | 6–1, 6–2 |
| Open Gaz de France Paris, France Tier II Hard, outdoor 22–28 February 1999 | 62 | 2R | Nathalie Tauziat | #9 | Win | 6–1, 6–4 |
| Open Gaz de France Paris, France Tier II Hard, outdoor 22–28 February 1999 | 63 | QF | Julie Halard-Decugis | #21 | Win | 6–2, 6–3 |
| Open Gaz de France Paris, France Tier II Hard, outdoor 22–28 February 1999 | 64 | SF | Nathalie Dechy | #43 | Win | 6–1, 6–4 |
| Open Gaz de France Paris, France Tier II Hard, outdoor 22–28 February 1999 | 65 | F | Amélie Mauresmo | #18 | Win | 6–2, 3–6, 7–6$^{(7–4)}$ |
| Evert Cup Indian Wells, USA Tier I Hard, outdoor 1–14 March 1999 | 66 | 1R | Jessica Steck | #230 | Win | 6–1, 7–5 |
| Evert Cup Indian Wells, USA Tier I Hard, outdoor 1–14 March 1999 | 67 | 2R | Lindsay Davenport | #2 | Win | 6–4, 6–2 |
| Evert Cup Indian Wells, USA Tier I Hard, outdoor 1–14 March 1999 | 68 | 3R | Cara Black | #36 | Win | 6–0, 7–5 |
| Evert Cup Indian Wells, USA Tier I Hard, outdoor 1–14 March 1999 | 69 | QF | Mary Pierce | #8 | Win | 7–5, 7–6$^{(7–1)}$ |
| Evert Cup Indian Wells, USA Tier I Hard, outdoor 1–14 March 1999 | 70 | SF | Sandrine Testud | #14 | Win | 7–5, 6–0 |
| Evert Cup Indian Wells, USA Tier I Hard, outdoor 1–14 March 1999 | 71 | F | Steffi Graf | #7 | Win | 6–3, 3–6, 7–5 |
| Lipton Championships Miami, USA Tier I Hard, outdoor 15–28 March 1999 | - | 1R | Bye | Bye | Bye | Bye |
| Lipton Championships Miami, USA Tier I Hard, outdoor 15–28 March 1999 | 72 | 2R | Alicia Molik | #107 | Win | 6–2, 6–3 |
| Lipton Championships Miami, USA Tier I Hard, outdoor 15–28 March 1999 | 73 | 3R | Magüi Serna | #25 | Win | 6–3, 6–2 |
| Lipton Championships Miami, USA Tier I Hard, outdoor 15–28 March 1999 | 74 | 4R | Monica Seles | #3 | Win | 6–2, 6–3 |
| Lipton Championships Miami, USA Tier I Hard, outdoor 15–28 March 1999 | 75 | QF | Amanda Coetzer | #9 | Win | 6–4, 6–0 |
| Lipton Championships Miami, USA Tier I Hard, outdoor 15–28 March 1999 | 76 | SF | Martina Hingis | #1 | Win | 6–4, 7–6$^{(7–3)}$ |
| Lipton Championships Miami, USA Tier I Hard, outdoor 15–28 March 1999 | 77 | F | Venus Williams | #6 | Loss | 6–1, 4–6, 6–4 |
| Italian Open Rome, Italy Tier I Clay, outdoor 3–9 May 1999 | - | 1R | Bye | Bye | Bye | Bye |
| Italian Open Rome, Italy Tier I Clay, outdoor 3–9 May 1999 | 78 | 2R | Tatiana Panova | #71 | Win | 6–4, 6–1 |
| Italian Open Rome, Italy Tier I Clay, outdoor 3–9 May 1999 | 79 | 3R | Irina Spîrlea | #17 | Win | 6–2, 6–3 |
| Italian Open Rome, Italy Tier I Clay, outdoor 3–9 May 1999 | 80 | QF | Martina Hingis | #1 | Loss | 2–6, 2–6 |
| German Open Berlin, Germany Tier I Clay, outdoor 10–16 May 1999 | - | 1R | Bye | Bye | Bye | Bye |
| German Open Berlin, Germany Tier I Clay, outdoor 10–16 May 1999 | 81 | 2R | Jennifer Capriati | #115 | Win | 7–6$^{(7–3)}$, 6–3 |
| German Open Berlin, Germany Tier I Clay, outdoor 10–16 May 1999 | 82 | 3R | Lisa Raymond | #38 | Win | 6–1, 7–6$^{(7–1)}$ |
| German Open Berlin, Germany Tier I Clay, outdoor 10–16 May 1999 | 83 | QF | Arantxa Sánchez Vicario | #7 | Loss | 3–6, 2–3 Ret |
| French Open Paris, France Grand Slam Clay, outdoor 25 May – 7 June 1999 | 84 | 1R | Laurence Courtois | #99 | Win | 6–0, 6–4 |
| French Open Paris, France Grand Slam Clay, outdoor 25 May – 7 June 1999 | 85 | 2R | Mariana Díaz Oliva | #94 | Win | 6–3, 6–4 |
| French Open Paris, France Grand Slam Clay, outdoor 25 May – 7 June 1999 | 86 | 3R | Mary Joe Fernández | #37 | Loss | 3–6, 6–1, 0–6 |
| Fed Cup WG: USA vs. Italy Ancona, Italy Team Event Clay July 19–25, 1999 | 87 | – | Rita Grande | NR | Win | 6–1, 6–1 |
| Acura Classic Los Angeles, USA Tier II Hard 9–15 August 1999 | 88 | 1R | Elena Likhovtseva | #21 | Win | 4–6, 6–3, 6–1 |
| Acura Classic Los Angeles, USA Tier II Hard 9–15 August 1999 | 89 | 2R | Patty Schnyder | #19 | Win | 6–3, 6–1 |
| Acura Classic Los Angeles, USA Tier II Hard 9–15 August 1999 | 90 | QF | Arantxa Sánchez Vicario | #8 | Win | 6–2, 6–3 |
| Acura Classic Los Angeles, USA Tier II Hard 9–15 August 1999 | 91 | SF | Martina Hingis | #1 | Win | 6–3, 7–5 |
| Acura Classic Los Angeles, USA Tier II Hard 9–15 August 1999 | 92 | F | Julie Halard-Decugis | #16 | Win | 6–1, 6–4 |
| US Open New York City, USA Grand Slam Hard, outdoor 30 August – 12 September 1999 | 93 | 1R | Kimberly Po | #80 | Win | 6–1, 6–0 |
| US Open New York City, USA Grand Slam Hard, outdoor 30 August – 12 September 1999 | 94 | 2R | Jelena Kostanić | #128 | Win | 6–4, 6–2 |
| US Open New York City, USA Grand Slam Hard, outdoor 30 August – 12 September 1999 | 95 | 3R | Kim Clijsters | #98 | Win | 4–6, 6–2, 7–5 |
| US Open New York City, USA Grand Slam Hard, outdoor 30 August – 12 September 1999 | 96 | 4R | Conchita Martínez | #16 | Win | 4–6, 6–2, 6–2 |
| US Open New York City, USA Grand Slam Hard, outdoor 30 August – 12 September 1999 | 97 | QF | Monica Seles | #4 | Win | 4–6, 6–3, 6–2 |
| US Open New York City, USA Grand Slam Hard, outdoor 30 August – 12 September 1999 | 98 | SF | Lindsay Davenport | #2 | Win | 6–4, 1–6, 6–4 |
| US Open New York City, USA Grand Slam Hard, outdoor 30 August – 12 September 1999 | 99 | F | Martina Hingis | #1 | Win | 6–3, 7–6$^{(7–4)}$ |
| Grand Slam Cup Munich, Germany Exhibition Carpet,indoor 27 September – 3 October 1999 | 100 | QF | Arantxa Sánchez Vicario | #15 | Win | 6–3, 6–1 |
| Grand Slam Cup Munich, Germany Exhibition Carpet,indoor 27 September – 3 October 1999 | 101 | SF | Lindsay Davenport | #2 | Win | 6–3, 6–4 |
| Grand Slam Cup Munich, Germany Exhibition Carpet,indoor 27 September – 3 October 1999 | 102 | F | Venus Williams | #15 | Win | 6–1, 3–6, 6–3 |
| Porsche Tennis Grand Prix Filderstadt, Germany Tier II Hard, outdoor 4–10 October 1999 | - | 1R | Bye | Bye | Bye | Bye |
| Porsche Tennis Grand Prix Filderstadt, Germany Tier II Hard, outdoor 4–10 October 1999 | 103 | 2R | Sandrine Testud | #13 | Loss | 6–3, 4–6, 5–7 |

### Doubles matches

| Tournament | Match | Round | Partner | Opponents | Rank | Result | Score |
| Sydney International Sydney, Australia Tier II Hard, outdoor 11–17 January 1999 | 28 | 1R | Venus Williams | Amanda Coetzer Natasha Zvereva | #25 #1 | Win | 7–5, 7–5 |
| Sydney International Sydney, Australia Tier II Hard, outdoor 11–17 January 1999 | 29 | QF | Venus Williams | Inés Gorrochategui Conchita Martínez | #99 #16 | Win | 6–4, 6–1 |
| Sydney International Sydney, Australia Tier II Hard, outdoor 11–17 January 1999 | 30 | SF | Venus Williams | Mary Joe Fernández Anke Huber | #78 #70 | Loss | 7–6$^{(9–7)}$, 5–7, 5–7 |
| Australian Open Melbourne, Australia Grand Slam Hard, outdoor 18–31 January 1999 | 31 | 1R | Venus Williams | Catherine Barclay-Reitz Kerry-Anne Guse | #44 #29 | Win | 6–4, 6–1 |
| Australian Open Melbourne, Australia Grand Slam Hard, outdoor 18–31 January 1999 | 32 | 2R | Venus Williams | Christina Singer Helena Vildová | #114 #86 | Win | 6–3, 6–1 |
| Australian Open Melbourne, Australia Grand Slam Hard, outdoor 18–31 January 1999 | 33 | 3R | Venus Williams | Mariaan de Swardt Elena Tatarkova | #16 #21 | Win | 7–6$^{(7–3)}$, 6–2 |
| Australian Open Melbourne, Australia Grand Slam Hard, outdoor 18–31 January 1999 | 34 | QF | Venus Williams | Arantxa Sánchez Vicario Larisa Neiland | #12 #10 | Win | 6–4, 4–6, 6–1 |
| Australian Open Melbourne, Australia Grand Slam Hard, outdoor 18–31 January 1999 | 35 | SF | Venus Williams | Lindsay Davenport Natasha Zvereva | #4 #1 | Loss | 6–1, 4–6, 4–6 |
| Faber Grand Prix Hanover, Germany Tier II Hard, indoorS 15–22 February 1999 | 36 | 1R | Venus Williams | Elena Wagner Anne-Gaëlle Sidot | #89 #59 | Win | 6–1, 6–1 |
| Faber Grand Prix Hanover, Germany Tier II Hard, indoorS 15–22 February 1999 | 37 | QF | Venus Williams | Manon Bollegraf Caroline Vis | #19 #14 | Win | 6–1, 6–4 |
| Faber Grand Prix Hanover, Germany Tier II Hard, indoorS 15–22 February 1999 | 38 | SF | Venus Williams | Elena Likhovtseva Ai Sugiyama | #11 #15 | Win | 6–2, 7–6$^{(10–8)}$ |
| Faber Grand Prix Hanover, Germany Tier II Hard, indoorS 15–22 February 1999 | 39 | F | Venus Williams | Alexandra Fusai Nathalie Tauziat | #9 #8 | Win | 5–7, 6–2, 6–2 |
| Evert Cup Indian Wells, USA Tier I Hard, outdoor 1–14 March 1999 | 40 | 1R | Venus Williams | Katrina Adams Debbie Graham | #33 #34 | Win | 6–0, 6–1 |
| Evert Cup Indian Wells, USA Tier I Hard, outdoor 1–14 March 1999 | 41 | 2R | Venus Williams | Silvia Farina Elia Linda Wild | #22 #196 | Win | 4–6, 6–2, 6–2 |
| Evert Cup Indian Wells, USA Tier I Hard, outdoor 1–14 March 1999 | 42 | QF | Venus Williams | Lindsay Davenport Natasha Zvereva | #4 #1 | Win | 4–6, 6–2, 6–3 |
| Evert Cup Indian Wells, USA Tier I Hard, outdoor 1–14 March 1999 | 43 | SF | Venus Williams | Mary Joe Fernández Jana Novotná | #50 #3 | Loss | 3–6, 4–6 |
| Lipton Championships Miami, USA Tier I Hard, outdoor 15–28 March 1999 | – | 1R | Bye | Bye | Bye | Bye |
| Lipton Championships Miami, USA Tier I Hard, outdoor 15–28 March 1999 | 44 | 2R | Venus Williams | Debbie Graham Rita Grande | #35 #102 | Win | 6–4, 7–5 |
| Lipton Championships Miami, USA Tier I Hard, outdoor 15–28 March 1999 | – | 3R | Venus Williams | Silvia Farina Elia Karina Habšudová | #33 #37 | Withdrew | N/A |
| French Open Paris, France Grand Slam Clay, outdoor 24 May – 6 June 1999 | 45 | 1R | Venus Williams | Amanda Coetzer Inés Gorrochategui | #41 #78 | Win | 6–2, 6–3 |
| French Open Paris, France Grand Slam Clay, outdoor 24 May – 6 June 1999 | 46 | 2R | Venus Williams | Amy Frazier Katie Schlukebir | #72 #56 | Win | 6–3, 6–2 |
| French Open Paris, France Grand Slam Clay, outdoor 24 May – 6 June 1999 | 47 | 3R | Venus Williams | Vanessa Menga Elena Wagner | #112 #99 | Win | 6–1, 6–3 |
| French Open Paris, France Grand Slam Clay, outdoor 24 May – 6 June 1999 | 48 | QF | Venus Williams | Els Callens Rita Grande | #33 #88 | Win | 6–0, 7–5 |
| French Open Paris, France Grand Slam Clay, outdoor 24 May – 6 June 1999 | 49 | SF | Venus Williams | Lindsay Davenport Mary Pierce | #4 #53 | Win | 6–4, 6–1 |
| French Open Paris, France Grand Slam Clay, outdoor 24 May – 6 June 1999 | 50 | F | Venus Williams | Martina Hingis Anna Kournikova | #2 #5 | Win | 6–3, 6–7$^{(2–7)}$, 8–6 |
| Fed Cup WG: USA vs. Italy Ancona, Italy Team Event Clay July 19–25, 1999 | 51 | – | Venus Williams | Tathiana Garbin Adriana Serra Zanetti | #187 #207 | Win | 6–2, 6–2 |
| TIG Tennis Classic San Diego, USA Tier II Hard 2–8 August 1999 | 52 | 1R | Venus Williams | Tina Križan Katarina Srebotnik | #52 #33 | Win | 1–6, 6–2, 6–2 |
| TIG Tennis Classic San Diego, USA Tier II Hard 2–8 August 1999 | 53 | QF | Venus Williams | Cara Black Cătălina Cristea | #28 #60 | Win | 6–2, 6–3 |
| TIG Tennis Classic San Diego, USA Tier II Hard 2–8 August 1999 | 54 | SF | Venus Williams | Elena Likhovtseva Ai Sugiyama | #7 #12 | Win | 6–2, 6–0 |
| TIG Tennis Classic San Diego, USA Tier II Hard 2–8 August 1999 | 55 | F | Venus Williams | Lindsay Davenport Corina Morariu | #3 #17 | Loss | 4–6, 1–6 |
| US Open New York City, USA Grand Slam Hard, outdoor 30 August – 12 September 1999 | 56 | 1R | Venus Williams | Miho Saeki Yuka Yoshida | #57 #56 | Win | 6–2, 6–3 |
| US Open New York City, USA Grand Slam Hard, outdoor 30 August – 12 September 1999 | 57 | 2R | Venus Williams | Amanda Coetzer Inés Gorrochategui | #38 #67 | Win | 6–7$^{(6–8)}$, 6–4, 6–4 |
| US Open New York City, USA Grand Slam Hard, outdoor 30 August – 12 September 1999 | 58 | 3R | Venus Williams | Linda Wild Nana Smith | #69 #72 | Win | 6–4, 6–1 |
| US Open New York City, USA Grand Slam Hard, outdoor 30 August – 12 September 1999 | 59 | QF | Venus Williams | Mary Joe Fernández Monica Seles | #23 #24 | Win | 6–3, 6–3 |
| US Open New York City, USA Grand Slam Hard, outdoor 30 August – 12 September 1999 | 60 | SF | Venus Williams | Mary Pierce Barbara Schett | #22 #32 | Win | 7–6$^{(7–2)}$, 6–3 |
| US Open New York City, USA Grand Slam Hard, outdoor 30 August – 12 September 1999 | 61 | F | Venus Williams | Chanda Rubin Sandrine Testud | #51 #68 | Win | 6–3, 7–6$^{(7–4)}$ |
| Fed Cup WG: USA vs. Russia Stanford Team Event Clay September 13–19, 1999 | 62 | – | Venus Williams | Elena Dementieva Elena Makarova | #NA #330 | Win | 6–2, 6–1 |

### Mixed doubles matches

| Tournament | Match | Round | Partner | Opponents | Rank | Result | Score |
| Australian Open Melbourne, Australia Grand Slam Hard, outdoor 18–30 January 1999 | 18 | 1R | Max Mirnyi | Rennae Stubbs Jim Grabb | #5 #18 | Win | 6–1, 7–6$^{(7–2)}$ |
| Australian Open Melbourne, Australia Grand Slam Hard, outdoor 18–30 January 1999 | 19 | 2R | Max Mirnyi | Elena Likhovtseva Jeff Tarango | #9 #53 | Win | 6–4, 6–4 |
| Australian Open Melbourne, Australia Grand Slam Hard, outdoor 18–30 January 1999 | 20 | QF | Max Mirnyi | Els Callens Chris Haggard | #45 #47 | Win | 6–3, 6–4 |
| Australian Open Melbourne, Australia Grand Slam Hard, outdoor 18–30 January 1999 | 21 | SF | Max Mirnyi | Manon Bollegraf Pablo Albano | #18 #51 | Win | 6–4, 6–4 |
| Australian Open Melbourne, Australia Grand Slam Hard, outdoor 18–30 January 1999 | 22 | F | Max Mirnyi | Mariaan de Swardt David Adams | #16 #34 | Loss | 6–4, 4–6, 7–6$^{(7–5)}$ |

## Tournament schedule
### Singles schedule

Williams' 1999 singles tournament schedule is as follows:
| Date | Championship | Location | Category | Surface | Points | Outcome |
| 11 January 1999– 17 January 1999 | Sydney International | Sydney (AUS) | WTA Tier II | Hard | 26 | Second Round lost to Steffi Graf 2–6, 6–3, 5–7 |
| 18 January 1999– 31 January 1999 | Australian Openl | Melbourne (AUS) | Grand Slam | Hard | 44 | Third Round lost to Sandrine Testud 2–6, 6–2, 7–9 |
| 22 February 1999– 28 February 1999 | Open Gaz de France | Paris (FRA) | WTA Tier II | Hard | 200 | Winner defeated Amélie Mauresmo 6–2, 3–6, 7–6$^{(7–4)}$ |
| 1 March 1999– 14 March 1999 | Evert Cup | Indian Wells (USA) | WTA Tier I | Hard | 260 | Winner defeated Steffi Graf 6–3, 3–6, 7–5 |
| 15 March 1999– 28 March 1999 | Lipton Championships | Miami (USA) | WTA Tier I | Hard | 182 | Final lost to Venus Williams 6–1, 4–6, 6–4 |
| 3 May 1999– 9 May 1999 | Italian Open | Rome (ITA) | WTA Tier I | Clay | 65 | Quarterfinals lost to Martina Hingis 2–6, 2–6 |
| 10 May 1999– 16 May 1999 | German Open | Berlin (GER) | WTA Tier I | Clay | 65 | Quarterfinals lost to Arantxa Sánchez Vicario 3–6, 2–3 Ret |
| 24 May 1999– 6 June 1999 | French Open | Paris (FRA) | Grand Slam | Clay | 44 | Third Round lost to Mary Joe Fernández 3–6, 6–1, 0–6 |
| 19 July 1999– 25 July 1999 | Fed Cup World Group: Italy vs. United States | Ancona (ITA) | Fed Cup | Clay | | United States def. Italy, 4–1 United States Advanced to Fed Cup Final |
| 9 August 1999– 15 August 1999 | Acura Classic | Los Angeles (USA) | WTA Tier II | Hard | 200 | Winner defeated Julie Halard-Decugis 6–1, 6–4 |
| 30 August 1999– 12 September 1999 | US Open | New York City (USA) | Grand Slam | Hard | 520 | Winner defeated Martina Hingis 6–3, 7–6$^{(7–4)}$ |
| 27 September 1999– 3 October 1999 | Grand Slam Cup | Munich (GER) | Exhibition | Carpet (i) | | Winner defeated Venus Williams 6–1, 3–6, 6–3 |
| 4 October 1999– 10 October 1999 | Porsche Tennis Grand Prix | Filderstadt (GER) | WTA Tier II | Hard | 1 | Second Round lost to Sandrine Testud 6–3, 4–6, 5–7 |
| 1999 Total year-end points | 1999 Total year-end points | 1999 Total year-end points | 1999 Total year-end points | 1999 Total year-end points | 1607 | |

### Doubles schedule

Williams' 1999 doubles tournament schedule is as follows:
| Date | Championship | Location | Category | Partner | Surface | Points | Outcome |
| 11 January 1999– 17 January 1999 | Sydney International | Sydney (AUS) | WTA Tier II | Venus Williams | Hard | 90 | Semifinals lost to Fernández/Huber 7–6$^{(9–7)}$, 5–7, 5–7 |
| 18 January 1999– 31 January 1999 | Australian Openl | Melbourne (AUS) | Grand Slam | Venus Williams | Hard | 234 | Semifinals lost to Davenport/Zvereva 6–1, 4–6, 4–6 |
| 15 February 1999– 21 February 1999 | Faber Grand Prix | Hanover (GER) | WTA Tier II | Venus Williams | Hard (i) | 200 | Winner defeated Fusai/Tauziat 5–7, 6–2, 6–2 |
| 1 March 1999– 14 March 1999 | Evert Cup | Indian Wells (USA) | WTA Tier I | Venus Williams | Hard | 117 | Semifinals lost to Fernández/Novotná 3–6, 4–6 |
| 15 March 1999– 28 March 1999 | Lipton Championships | Miami (USA) | WTA Tier I | Venus Williams | Hard | 36 | Third Round Withdrew against Elia/Habšudová |
| 24 May 1999– 6 June 1999 | French Open | Paris (FRA) | Grand Slam | Venus Williams | Clay | 520 | Winner defeated Hingis/Kournikova 6–3, 6–7$^{(2–7)}$, 8–6 |
| 19 July 1999– 25 July 1999 | Fed Cup World Group: Italy vs. United States | Ancona (ITA) | Fed Cup | Venus Williams | Clay | | United States def. Italy, 4–1 United States Advanced to Fed Cup Final |
| 2 August 1999– 8 August 1999 | TIG Tennis Classic | San Diego (USA) | WTA Tier II | Venus Williams | Hard | 140 | Final lost to Davenport/Morariu 4–6, 1–6 |
| 30 August 1999– 12 September 1999 | US Open | New York City (USA) | Grand Slam | Venus Williams | Hard | 520 | Winner defeated Rubin/Testud 6–3, 7–6$^{(7–4)}$ |
| 19 July 1999– 25 July 1999 | Fed Cup World Group: United States vs. Russia | Stanford (USA) | Fed Cup | Venus Williams | Clay | | United States def. Russia, 4–1 United States Wins Fed Cup Title |
| 1999 Total year-end points | 1999 Total year-end points | 1999 Total year-end points | 1999 Total year-end points | 1999 Total year-end points | 1999 Total year-end points | 2117 | |

### Mixed doubles schedule

Williams' 1999 doubles tournament schedule is as follows:
| Date | Championship | Location | Category | Partner | Surface | Outcome |
| 18 January 1999- 30 January 1999 | Australian Open | Melbourne (AUS) | Grand Slam | Max Mirnyi | Hard | Final lost to de Swardt/ Adams 6–4, 4–6, 7–6$^{(7–5)}$ |

## Yearly records
### Head-to-head matchups

* Lindsay Davenport 3–0
* Julie Halard-Decugis 2–0
* Magüi Serna 2–0
* Monica Seles 2–0
* Inés Gorrochategui 1-0
* Raluca Sandu 1–0
* Åsa Svensson 1–0
* Nathalie Tauziat 1–0
* Lisa Raymond 1-0
* Kimberly Po 1–0
* Jelena Kostanić 1–0
* Laurence Courtois 1–0
* Nathalie Dechy 1–0
* Amélie Mauresmo 1–0
* Jessica Steck 1–0
* Cara Black 1–0
* Mary Pierce 1–0
* Alicia Molik 1–0
* Amanda Coetzer 1–0
* Jennifer Capriati 1–0
* Kim Clijsters 1–0
* Conchita Martínez 1–0
* Rita Grande 1–0
* Mariana Díaz Oliva 1–0
* Tatiana Panova 1–0
* Irina Spîrlea 1–0
* Elena Likhovtseva 1–0
* Patty Schnyder 1–0
* Venus Williams 1–1
* Steffi Graf 1-1
* Martina Hingis 3–1
* Arantxa Sánchez Vicario 2–1
* Sandrine Testud 1–2
* Mary Joe Fernández 0–1

### Finals
#### Singles: 6 (5–1)

* Winner — Legend
* Grand Slam tournaments (1–0)
* Grand Slam Cup (1–0)
* Tier I (1–1)
* Tier II (2–0)
* Finals by Surface
* Hard (4–1)
* Carpet (1–0)
* Finals by Surface
* Outdoors (4–1)
* Indoors (1–0)
| Outcome | No. | Date | Championship | Surface | Opponent | Score |
| Winner | 1. | February 28, 1999 | Paris, France (1) | Carpet | Amélie Mauresmo | 6–2, 3–6, 7–6$^{(7–4)}$ |
| Winner | 2. | March 14, 1999 | Indian Wells, US (1) | Hard | Steffi Graf | 6–3, 3–6, 7–5 |
| Runner-up | 1. | March 29, 1999 | Miami, US (1) | Hard | Venus Williams | 2–6, 6–4, 4–6 |
| Winner | 3. | August 15, 1999 | Los Angeles, US (1) | Hard | Julie Halard-Decugis | 6–1, 6–4 |
| Winner | 4. | September 12, 1999 | US Open, New York City, US (1) | Hard | Martina Hingis | 6–3, 7–6$^{(7–4)}$ |
| Winner | 5. | October 3, 1999 | Grand Slam Cup, Germany (1) | Hard | Venus Williams | 6–1, 3–6, 6–3 |

#### Doubles: 4 (3–1)

* Legend
* Grand Slam tournaments (2–0)
* Tier II (1–1)
* Finals by Surface
* Hard (1–1)
* Carpet (1–0)
* Clay (1–0)
* Finals by Surface
* Outdoors (2–1)
* Indoors (1–0)
| Outcome | No. | Date | Championship | Surface | Partner | Opponent | Score |
| Winner | 3. | February 15, 1999 | Hanover, Germany (1) | Carpet | Venus Williams | Alexandra Fusai Nathalie Tauziat | 5–7, 6–2, 6–2 |
| Winner | 4. | May 24, 1999 | French Open, Paris, France (1) | Clay | Venus Williams | Martina Hingis Anna Kournikova | 6–3, 6–7$^{(2–7)}$, 8–6 |
| Runner-up | 1. | August 8, 1999 | San Diego, US (1) | Hard | Venus Williams | Lindsay Davenport Corina Morariu | 6–4, 6–1 |
| Winner | 5. | August 30, 1999 | US Open, New York City, US (1) | Hard | Venus Williams | Chanda Rubin Sandrine Testud | 4–6, 6–1, 6–4 |

#### Mixed doubles: (0-1)

* Legend
* Grand Slam (0–1)
* Finals by Surface
* Hard (0–1)
| Outcome | No. | Date | Championship | Surface | Partner | Opponent | Score |
| Runner-up | 2. | September 12, 1999 | Australian Open | Hard | Max Mirnyi | David Adams Mariaan de Swardt | 6–4, 4–6, 7–6$^{(7–5)}$ |

### Earnings

| # | Event | Prize money | Year-to-date |
| 1 | Sydney International | $5,450 | $5,450 |
| 1 | Sydney International (doubles) | $3,100 | $8,550 |
| 2 | Australian Open | $14,575 | $23,125 |
| 2 | Australian Open (doubles) | $18,934 | $42,059 |
| 3 | Faber Grand Prix (doubles) | $12,750 | $54,809 |
| 4 | Open Gaz de France | $80,000 | $134,809 |
| 5 | Evert Cup | $215,000 | $349,809 |
| 5 | Evert Cup (doubles) | $8,850 | $358,659 |
| 6 | Lipton Championships | $132,000 | $490,659 |
| 6 | Lipton Championships (doubles) | $3,138 | $493,797 |
| 7 | Italian Open | $16,000 | $509,797 |
| 8 | German Open | $16,000 | $525,797 |
| 9 | French Open | $20,990 | $546,787 |
| 9 | French Open (doubles) | $99,268 | $646,055 |
| 10 | Acura Classic | $80,000 | $726,055 |
| 11 | TIG Tennis Classic (doubles) | $6,500 | $732,555 |
| 12 | US Open | $750,000 | $1,482,555 |
| 12 | US Open (doubles) | $165,000 | $1,647,555 |
| 13 | Grand Slam Cup | $900,000 | $2,547,555 |
| 14 | Porsche Tennis Grand Prix | $3,700 | $2,551,255 |
| Bonus Pool | Bonus Pool | $27,593 | $2,605,102 |
| | | | $2,605,102 |
Figures in United States dollars (USD) unless noted.