Serena Williams won her first U.S. Open as a 17-year-old in 1999. (Jamie Squire/Allsport)

Serena Williams and Arthur Ashe Stadium go back. Way back.

The 23-time Grand Slam champion is expected to retire from tennis following the 2022 US Open — a fitting cap to her career, as the New York tournament provided the setting for her first major title back in 1999.

But don’t count her out in her swan song.

Williams has won her first two matches, including an upset victory Wednesday against No. 2 seed Anett Kontaveit in the second round. She advances to face Ajla Tomljanović on Friday in the round of 32.

As Williams eyes another electric run at Arthur Ashe Stadium, Just Women’s Sports takes a look back at her six previous US Open championships.

1999: A star is born

A teenager entered the 1999 final as the world No. 1 and a five-time major champion – and it wasn’t Williams. Martina Hingis entered as the seasoned veteran at all of 18 years old, while 17-year-old Williams came in as the upstart looking for her first major victory.

The No. 7 seed, Williams faced off against four eventual Hall of Famers on the way to the final: Kim Clijsters, Conchita Martinez, Monica Seles and finally No. 2 seed Lindsay Davenport in the semifinals.

In the championship match, Williams won in straight sets, 6-3, 7-6 (9-7), announcing herself as a star in her own right. She even beat older sister Venus to a major title – Venus won her first two in 2000 at Wimbledon and back at the US Open.

“Even though Richard Williams had already been making noise about how Serena ultimately was going to be the better player, better than Venus, we didn’t think it was going to happen quite yet,” Hall of Fame tennis journalist Steve Fink told USOpen.org. “I just remember it really surprised me. A year or two later it wouldn’t have, but I thought Martina was still going to have the edge at that stage in the final, with her experience.”

2002: The Venus and Serena Show

After winning her first US Open, Williams did not win another major until 2002 – but that year, she went on a tear. She won the French Open and Wimbledon before capping her year with another win in New York, and all three titles came against sister Venus.

She blazed through the year’s last major. In her first five matches, she conceded just 14 games through 10 sets, then dispatched No. 4 seed Davenport in straight sets in the semifinal. Finally, the younger Williams sister then took down the elder 6-4, 6-3.

“Serena was the best player the whole tournament this year,” Venus said at the time. “I have to give it to her for that. My game went down after the fourth round and I just couldn’t do a thing to bring it back up.”

(Bongarts/Getty Images)

This major saw Serena turn heads not just for her play but also for her fashion sense. The now infamous catsuit, designed by Puma, drew worldwide attention following her first match.

“If you don’t have a decent shape, this isn’t the outfit to have,” Williams said. “It makes me run faster and jump higher and it’s really sexy. [Venus told me it’s] really fun, really exciting and very sexy. I mean, she just basically described me.”

While Williams received blowback for the outfit, she shut down the critics, saying, “Nobody is ever going to tell me what to wear.”

(Gary M. Prior/Getty Images)

2008: Reclaimed glory

Williams reached No. 1 in the world for the first time in 2002, but she lost the ranking in 2003. She didn’t regain the top spot again until her third US Open win in 2008.

Entering as the No. 4 seed, Williams did not drop a set en route to the title. Her most troublesome match of the tournament came in the quarterfinals against Venus, who took Serena to tiebreakers in both sets.

From there, Williams sailed through the semifinal against Dinara Safina and the final against Jelena Jankovic.

While she walked away with her ninth major, Williams asserted after the match that she wasn’t satisfied. Of course, she eventually compiled a total of 23 Grand Slam singles titles.

“I’m pushing the doors to double digits, which I obviously want to get to,” she said. “I feel like I can do it.”

2012: 30 and thriving

With her win over Victoria Azarenka in 2012, Williams became the third woman in history to win Wimbledon, the US Open and the Olympics in the same season, joining Steffi Graf (1988) and sister Venus (2000).

The world No. 1 made a near-flawless run, with her only lost set coming in the final against Azarenka, which she won 6-2, 2-6, 7-5. Williams served up 13 total aces in the final and hit a peak serve of 125 mph at one point in the match.

Despite her dominant play, Williams found herself on the verge of defeat – two points away from it, in fact – before she rallied to take the final four games and win the final set.

After winning her 15th major at the age of 30, Williams would rattle off another eight majors in her 30s.

2013: Back-to-back titles

The duo of Azarenka and Williams met once again in the US Open final, and once again, it was a three-set thriller, with Williams winning 7-5, 6-7 (10-8), 6-1. In another repeat of the previous year, Williams’ lone dropped set came against Azarenka in the final.

The 2013 major marked the 17th of her career, officially beginning the chants proclaiming Williams to be the greatest of all time. It also marked her fourth major in 16 months, a record for a women’s player over the age of 30.

Five majors away from Steffi Graf’s record of 22 in the Open era, 32-year-old Williams shut down questions about age as an obstacle to her success.

“I don’t think about it. I always said, age for me, I feel great. I’ve never felt better,” she said. “I feel really fit. I haven’t felt like this in a number of years, and so I’m excited about the possibilities.

“I don’t know what can happen, I just keep playing and doing the best that I can.”

Of course, Williams would go on to win six more majors. Further defying the doubters, Williams would make the final at both Wimbledon and the US Open in 2018 mere months after giving birth to daughter Olympia Ohanian.

2014: Three-peat for the ages

Williams won her third consecutive US Open in 2014, just one off the record of Chris Evert, who rattled off four in a row from 1975-78. For a record-matching third time, she did not lose a set en route to the title.

She also equaled the record for US Open singles titles in the Open era.

In the final, Williams took down friend Caroline Wozniacki, 6-3, 6-1. The match lasted just 75 minutes, and Williams was emotional as she accepted the trophy on the same court on which she won her first at 17 years old.

(Matthew Stockman/Getty Images)

“It is a pleasure for me to win my first Grand Slam here and then this No. 18,” Williams said. “So I’m really emotional. I couldn’t ask to do it at a better place.”

For her win, Williams won a record $4 million – $3 million in prize money plus $1 million as a bonus for having the best record during the North America summer hard court circuit. The match also made her the first women’s athlete to earn more than $60 million in prize money.