Serena and Venus Williams dominated the US Open in the early 2000’s to cement their legacy in the history of tennis.

Serena retired at the US Open in 2022, having won six of her 23 Grand Slam titles at her home major.

Despite being the older sister, 44-year-old Venus Williams is yet to officially retire, but has not competed since the 2024 Miami Open where she lost in straight sets to Diana Shnaider.

The Williams sisters were often compared to one another, including at the 1999 US Open when Martina Hingis had to play them in back-to-back matches.

11 Sep 1999: Serena Williams of the USA and Martina Hingis of Switzerland smile and pose with their trophies after their match in the US Open at t…

Martina Hingis says who was better out of Serena and Venus Williams at the 1999 US Open

At this stage in time, neither Williams sister had won a Grand Slam title and Serena was only 17-years-old heading into the 1999 US Open.

While Hingis, who was still a teenager herself, had already won six Grand Slam titles prior to this tournament.

Three of these major titles all came at one event, with Hingis defending the Australian Open twice.

Photo by Simon Bruty/Anychance/Getty Images
Although she had never made it past the fourth round of a Grand Slam before, Serena found herself in the US Open final after winning four consecutive three set matches.

This included coming from 5-3 down in the deciding set of her third round match against fellow teenager and future Grand Slam champion Kim Clijsters.

On the other hand, top seed Hingis only had to play one three set match at the 1999 US Open against Serena’s older sister, Venus, in the semi-final.

Hingis would overcome Venus in her semi-final, but Serena was one Williams sister too many as she lifted her first of what has since become six US Open singles titles.

Round
Serena Williams
Martina Hingis

First Round
Beat Kimberly Po, 6-1 6-0
Beat Kveta Hrdlickova, 6-1 7-5

Second Round
Beat Jelena Kostanic, 6-4 6-2
Beat Sarah Pitkowski, 6-1 6-1

Third Round
Beat Kim Clijsters, 4-6 6-2 7-5
Beat Sandra Klosel, 6-3 6-1

Fourth Round
Beat Conchita Martinez (16), 4-6 6-2 6-2
Beat Arantxa Sanchez Vicario (10), 6-4 7-5

Quarter-final
Beat Monica Seles (4), 4-6 6-3 6-2
Beat Anke Huber, 6-2 6-0

Semi-final
Beat Lindsay Davenport (2), 6-4 1-6 6-4
Beat Venus Williams (3), 6-1 4-6 6-3

Final
Beat Martina Hingis (1), 6-3 7-6(4)
Lost to Serena Williams (7), 3-6 6(4)-7

In her press conference after the match, Hingis was asked whether she thought Serena was a better player than Venus.

While Hingis did not give a definitive answer, she pointed out the serve as a particular strength of Serena’s.

“It’s different. I mean, she [Serena] serves better definitely,” responded Hingis. “She puts more pressure on me like that. Also, I have to serve well. That’s probably the biggest, you know, thing in my game that I have to improve, to just be more consistent.

“Like even yesterday, I served like 74% of first serves. It wasn’t like an ace or anything. I have to definitely put more of those first serves in to just being able, you know, hang in those rallies. I know once I get into a rally at the end, I’m better. Once you don’t get there, it’s too bad.”

Martina Hingis on the challenges of playing Serena and Venus Williams in back-to-back matches

Having played Venus the evening prior, Hingis was questioned over whether this impacted her performance against Serena.

While she admitted to have a poor night’s sleep, Hingis acknowledged that Serena had played a lot more tennis leading into the final.

“Yeah, of course. But that was the same for both,” said Hingis. “She also had a three-setter. She actually had a harder tournament, too. She played more than I did. She also played doubles. I feel like, you know, we both were the same.

“I guess, you know, I had, like, a hard time also falling asleep. Just for me it was later, then coming out there today. But that’s no excuse. I mean, you just have to go out there and play. Well, it’s a tough schedule, you know, playing like the toughest matches at the end of the tournament like one after the other.

“It’s not so easy. I love CBS changing their request there Friday, Saturday. Just have to deal with it. Of course, I’m a bit disappointed. I mean, I had my chances; didn’t take them. There are many more years to come against the Williams’.”

Not only did Serena win the singles title that year, but alongside Venus also took victory in the US Open doubles event.

12 Sep 1999: Venus and Serena Williams of the USA pose with their trophy after the doubles match against Chanda Rubin of the USA and Sandrine Testu…
This year the New York major will begin on Sunday August 24, after the US Open was extended to 15 days for the first time.