Serena Williams played her 1000th career match against Nadia Podoroska in the second round of the 2021 Internazionali BNL d'Italia. To celebrate this milestone, we go down memory lane to look back at every 100th match the great champion has played in a career that spans four decades and multiple generations of rivalries.
100.  Serena Williams d. Arantxa Sánchez Vicario 6-3, 6-1, Grand Slam Cup, Munich first round, 27 Sep 1999
An ITF tournament that brought together the eight best Grand Slam performers of the year, the Grand Slam Cup was retroactively recognised as an official tournament by the WTA and ATP Tours. In its final year, it was a 17-year-old Serena's first destination after capturing her first major title at the US Open over Martina Hingis in her 99th match.
Serena opened against a nemesis of her early career. Four-time Grand Slam champion Arantxa Sánchez Vicario had won their first four meetings and would lead their final head-to-head 4-3. But 1999 had been a subpar year for the Spaniard, whose year-end ranking slid from World No.4 to World No.17. Serena had finally beaten her for the first time that year in Los Angeles, and on the slick Munich indoor carpet needed only 53 minutes to reprise that.
"She was making a lot of errors," said Serena afterwards. "It's not like I really won those first four games. Then she started playing a little better and I wasn't ready. When I started playing better, I started thinking, concentrating more, I was able to do better."
Serena went on to lift the trophy, beating older sister Venus for the first time in the final, to extend her winning streak to 16.
200.  Serena Williams d.  Jennifer Capriati 6-2, 4-6, 6-4, Scottsdale final, 25 Feb 2002
The arc of one of the most formative rivalries of Serena's career was not a pendulum swinging back and forth, but a reversal as she figured out and then conquered a formidable competitor. Jennifer Capriati won four of her first five matches against Serena in 2000-01 - and then Serena won the next eight, and ultimately nine of the last 12.
This was the second of the eight straight. Serena's defeat of Capriati in the 2001 Toronto final had started the turnaround, and arguably jumpstarted her career again. A sprained ankle had forced her out of the Australian Open - but, as this run to her 12th career title demonstrated, Serena had only been halted temporarily.
Serena followed Scottsdale by defeating Capriati again in the Miami final, and would embark on her first 'Serena Slam' at Roland Garros that year.
300.  Serena Williams d.  Eleni Daniilidou 6-4, 6-4, Miami semifinals, 24 Mar 2004
A month after Serena won her sixth Grand Slam title at Wimbledon 2003, she underwent left knee surgery. Initially expected to be out for six to eight weeks, recovery turned into an eight-month layoff with an ever-shifting return date. When she eventually stepped on court again, the rust barely showed. Miami 2004 was her first tournament back, and - ranked No.6 but seeded No.1 - she dropped only one set en route to her 24th trophy.
That was to Elena Likhovtseva in the third round, and Serena followed that with a straight-sets win over a 16-year-old Maria Sharapova in their first meeting. In the last four, she was pitted against rising Greek 21-year-old Eleni Daniilidou, who already had three WTA titles under her belt and who had taken out Jennifer Capriati en route to the biggest semifinal of her career. Daniilidou's all-court game and one-handed backhand weren't enough against Serena, though, despite the American dropping serve when trying to close out each set.
"I always expect the best of myself," said Serena afterwards. "I can't say that I didn't expect to reach the final. I do know what I didn't want to do is lose in the first round of my first tournament back. I wanted to have a steel, strong present."
400.  Serena Williams d.  Maria Sharapova 6-1, 6-1, Miami fourth round, 21 Mar 2007
2007 found Serena embarking on another comeback. During an injury-wracked 2006, she had played just four tournaments and finished the year ranked World No.95. That set the stage for one of her most iconic, and perhaps most unexpected, Grand Slam title run at the Australian Open, which culminated in a 6-1, 6-2 thrashing of Maria Sharapova.
Two months later, now ranked World No.18, Serena was even less generous. Prior to 2007, her head-to-head against Sharapova had been a nascent rivalry with two wins apiece. The Melbourne rout demonstrated how Serena's first-strike game could shut the Russian out completely, and backing it up in Miami en route to her 28th title underlined it.
"We've played each other a few times, and I like her game style," said Serena afterwards. "But next time it's going to be another tough battle. It's not going to be easy. I'm not going to go in there thinking, I've already won this. Not at all."
Serena may or may not have ever thought that, but the results would speak for themselves. Over the next 12 years, she would play Sharapova another 16 times - winning on every occasion, and dropping only two more sets.
500.  Serena Williams d.  Zheng Jie 6-4, 6-2, Dubai third round, 15 Feb 2009I
In February 2009, Serena was on top of the world again. She had won the two last majors at the 2008 US Open and 2009 Australian Open to take her total to 10, and that month had reclaimed the World No.1 ranking from Jelena Jankovic.
Zheng, too, was surging. The 25-year-old had become the first Chinese Grand Slam semifinalist at Wimbledon the previous year, and had also hit a personal milestone in February 2009 after breaking the Top 20. Zheng would never beat Serena in six meetings, and fell in straight sets for the third time here. But she would go on to be a worthy foil: their subsequent three meetings all went the distance, including high-quality classics at Miami 2009 and Wimbledon 2012.
During 2009, Serena mastered the art of peaking at the biggest events. Her only three titles were the Australian Open, Wimbledon and the WTA Finals. Her Dubai campaign was ended 6-1, 2-6, 7-6(3) by sister Venus in the semifinals.
600.  Serena Williams l.  Samantha Stosur 2-6, 3-6, US Open final, 29 Aug 2011
One of Serena's most shocking losses came in yet another comeback year. A foot injury sustained after stepping on broken glass in 2010, followed by a hematoma and pulmonary embolism, had sidelined her for just under 12 months.
But by now, the tennis world was used to Serena picking up after long layoffs as though she'd never been away. And despite her serious health issues, in 2011 she pulled it off again. After a rusty return in the grass swing, Serena compiled an 18-match winning streak on the North American hardcourts encompassing titles in Stanford and Toronto.
In New York, now ranked back at World No.27, she had been imperious, sweeping into the final without dropping a set via wins over Victoria Azarenka and Caroline Wozniacki. First-time US Open finalist Samantha Stosur had beaten Serena in a Grand Slam before, in the 2010 Roland Garros quarterfinals - but even then, Serena had held a match point, and she had defeated the Australian 6-4, 6-2 in the Toronto final three weeks before.
But Stosur came out and played arguably the match of her career to become the third player ever to defeat Serena in a Grand Slam final, following Venus Williams and Maria Sharapova.
"I really want to put it out there and gave all the credit to Sam today, because I think she played really well," said Serena. "I don't think she's ever played that well. Maybe she has. I haven't seen her play that well. But that's what you have to do. When you're in the final of a Grand Slam you have to do that."
700.  Serena Williams d.  Victoria Azarenka 6-1, 6-3, Rome final, 13 May 2013
2013 was arguably the most dominant season Serena has ever put together, capturing a career-best 11 titles and finishing with an astonishing 78-4 record. The jewel in her crown was her clay season. Having suffered her only first-round Grand Slam loss to Virginie Razzano at Roland Garros 2012, Serena bounced back to go unbeaten in 28 clay matches in 2013 (her red clay winning streak ultimately reached 32).
In Rome, Serena was spectacular. She dropped just 16 games in five matches en route to reclaiming a title she had not won since 2002. She did not lose more than three games in any given set. Victoria Azarenka, from whom she had reclaimed the World No.1 ranking in February that year, was responsible for two of Serena's four losses in 2013 - but could only muster four games in the final.
"It wasn't really easy out there," Serena said nonetheless. "Nothing is really easy. I just took the opportunities when I had them. I know she did as well, but I came up with the good shots sometimes."
800.  Serena Williams d.  Ana Ivanovic 6-4, 6-4, WTA Finals Singapore round robin, 20 Oct 2014
By the end of 2014, the Serena reign still hadn't let up. She had been World No.1 since February 2013, and would remain there until September 2016. Victory at the US Open had put her Grand Slam stumbles earlier in the season behind her, tying Martina Navratilova and Chris Evert on 18 major titles.
Illness and injury had cut short Serena's Wuhan and Beijing campaigns respectively. But in her opening round-robin match at the WTA Finals she demonstrated that she was still in superb form, defeating Ana Ivanovic for the fourth time in five matches that year and taking her WTA Finals winning streak to 16.
"They just happen," said Serena of her various streaks. "I'm aware of them because you guys make sure that I'm aware of them. I just found out last time that I was 15 matches and I was like, Oh, boy, not another streak. So now I'm 16 and, Gosh, here we go again. We'll see how it goes."
The streak was actually ended in Serena's next match, a stunning 6-0, 6-2 loss to Simona Halep. But she made it out of the group stages anyway - and inflicted a 6-3, 6-0 revenge on the Romanian in the final to seal her 64th career title, and fifth at the WTA Finals.
900.  Serena Williams d. [WC] Vania King 6-3, 6-3, US Open second round, 29 Aug 2016
In 2016, it felt as though Serena's main rival wherever she played was history. And she kept winning. At Wimbledon, she tied Stefanie Graf's Open Era record of 22 Grand Slam titles. Coming into the US Open, she was also assured of equalling Graf's record of 186 consecutive weeks at World No.1. And this second-round result enabled Serena to tie Martina Navratilova's record of 306 Grand Slam match wins - one that she immediately surpassed by reaching the semifinals.
"Sometimes I don't even know that I'm hitting these milestones," said Serena. "But some of them I'm really proud of. Like this one's kind of cool, to win 306. That's really a cool milestone. [Navratilova] was just an incredible legend. For me, one of the best players to ever play tennis. Someone that I never even thought I could be as good as numbers-wise."
The 2016 US Open also marked the end of Serena's No.1 reign, though. She lost to Karolina Pliskova in the semifinals, and Angelique Kerber's title run enabled the German to take over the top spot the following week. The 2017 Australian Open title saw Serena move ahead of Graf to hold the Open Era Grand Slam record by herself at 23. Just over a year after this match, she gave birth to daughter Olympia.
1000.  Serena Williams l. Nadia Podoroska 6-7(6), 5-7, Rome second round, 12 May 2021
Since returning from maternity leave in 2018, Serena's form had hit plenty of highs, but had never quite been able to shake off injury and consequent question marks. Four Grand Slam finals had been punctuated by spells on the sidelines, forcing her to shake off rust with each comeback.
That was the case in her 1000th match, which was Serena's first since losing to Naomi Osaka in the Australian Open semifinals three months previously. It was also just her second claycourt match since 2019. Serena faced a tough opponent in World No.44 Nadia Podoroska, the rising Argentinian who had become the first qualifier in the Open Era to reach the Roland Garros semifinals the previous year.
Serena showed her trademark fighting spirit, saving triple set point in the first-set tiebreak and reeling off 12 straight points from 2-5 down in the second set. But an inspired Podoroska didn't waver to close out her third career Top 10 win.