Serena Williams’s Most Memorable Matches at the U.S. Open

As the 23-time Grand Slam champion begins what is expected to be her final Slam event, we look back at her career in New York.

After 23 Grand Slam titles and 27 seasons since she became a professional tennis player, Serena Williams returned to the U.S. Open on Monday for what is expected to be the final major tournament of her career.

Williams holds many tennis records, but could she add to it by advancing far in this year’s tournament? Serena got off to a good start with her straight-sets, opening-round win against Danka Kovinić on Monday.

As fans begin to look back at Williams’s incredible career, we break down some of her most memorable matches in New York.

1999 Final: The Start of Serena Domination

Williams won her first Grand Slam title (one of six she’d wind up winning at the Open) in just her second appearance at the tournament. Serena, the seventh seed, took down No. 1 Martina Hingis 6–3, 7–6. At just 18 years old, a teenage superstar was born. Oh, and Venus and Serena also won the doubles title.

2001 Final: The Sister Rivalry Begins

Before their ’01 U.S. Open final meeting, the Williams sisters played each other five previous times on the tour, with Venus leading the series, 4–1. While they faced each other in earlier rounds of the Australian Open and Wimbledon, the sisters had never met in a Grand Slam final until 2001. Venus continued her dominance by beating Serena, 6–2, 6–4, in a match that was the first women’s tennis Grand Slam final to be shown on primetime television. The sisters would go on to face each other in eight more Grand Slam finals, with Serena leading 7–2 overall.

2002 Final: First Serena Slam

A lot changed for Serena by the time she faced Venus in 2002. She had captured two more Grand Slam titles at the French Open and Wimbledon earlier in the year, which helped her reach her first world No. 1 ranking. (When she played Venus in ’01, she was ranked No. 10.) As the No. 1 and No. 2 players in the world, Serena took down her sister for the third time that year in a 6–4, 6–3 win. Serena went on to win the ’03 Australian Open to finish off the first of two “Serena Slams” in her career.

2008 Quarterfinal: Iconic Sisters Match

The Williams sister rivalry continued as this match went down as one of the best, if not the best, matchup between them. Venus led both sets at different points, but couldn’t keep control. Serena, who held eight Grand Slam titles heading into the match, saved two set points and pushed both sets to a tiebreak. The younger Williams ended up winning both in a 7–6(6), 7–6(7) victory.

2008 Final: Back to Center Stage

Williams made it back to the main event in ’08 as a No. 4 seed in the tournament after not reaching the U.S. Open finals since ’02. After edging No. 2 Jelena Jankovic in a close 6–4, 7–5 victory, Williams’s celebration will go down as one of her most memorable.

2012 Final: Beginning of Azarenka Rivalry

After losing in the ’09 semifinals, missing the tournament in ’10 and falling in the ’11 final, Williams made her way back to the championship by beating one of her now-storied rivals, Victoria Azarenka, in their first Grand Slam final meeting. The American ended up beating the No. 1 player at the time in the three-set match 6–2, 2–6, 7–5.

2013 Final: Repeat Champion

The 2013 season was one of Williams’s most successful years. She won 11 titles, including the 2013 U.S. Open. She came into the final Grand Slam tournament of the year as the No. 1 seed and defending champion. In a repeat of the previous year’s final, Williams took down Azarenka, once again in three sets, 7–5, 6–7(6), 6–1. At 31, Williams became the oldest champion in the Open era. She won over $10 million, making her the first and only woman in tennis history to achieve the feat, and pushed her career earnings to over $50 million. She finished the year at No. 1 for the third time in her career, the oldest WTA player to rank No. 1.

2014 Final: Second Serena Slam

Williams’s 2014 run was one of the most dominating performances at a Grand Slam tournament, not dropping a single set en route to her 18th Slam title after a 6–3, 6–3, over Caroline Wozniacki in the final. It was her third straight Open title and 18th Slam win overall, tying her with Chris Evert and Martina Navratilova. Williams went on to win the Australian Open, French Open and Wimbledon in 2015. She ended up losing in the U.S. Open semifinals that year to just fall short of a Calendar Slam.

2018 Quarterfinals: Dominating on the Court as a Mother

After missing the ’17 U.S. Open as she prepared for the birth of her daughter, Serena returned to the court later in the year and continued to dominate. She won the 2018 French Open and reached the Wimbledon finals, and went on to have another successful run in New York. One of her most memorable matches came in the quarterfinals, where she beat Karolína Plíšková 6–4,6–3. Plíšková knocked out WIlliams in the ’16 U.S. Open semifinals and cost Williams a shot at the Calendar Slam and year-end No. 1 ranking.

It was also Williams’s first win against a top 10 player since she returned from her maternity leave and gave her the extra confidence she needed for another Grand Slam final. She ended up losing to Naomi Osaka in a controversial match.

2019 Semifinal: Record-Breaking Run

Shortly after reaching the Wimbledon final earlier in the year, Williams started off strong in New York. Her quarterfinal win marked her 100th at the Grand Slam tournament. She went on to face No. 5 Elina Svitolina in the semifinals and advanced to the final with a 6–3, 6–1 win. Williams ended up losing to No. 15 Bianca Andreescu in two sets. The final was the last time Serena appeared in a Grand Slam final.