Getty Images

Over twenty years ago, the sport of tennis was changed forever by two sisters from Compton, Calif. Ever since Serena Williams and Venus Williams burst onto the professional tennis scene in the late '90s, the pair of superstar siblings have transcended the sport of tennis. Between the two of them, the Williams sisters have won 30 Grand Slam titles (Serena with 23, Venus with seven). When playing doubles together, they've won 14 Grand Slam titles and three Olympic gold medals.

Their separate dominance has led to the pair facing each other 30 times. Serena holds the advantage at 18-12 for the rivalry that dates back to 1998. In the Grand Slam tournaments, Serena has 11 wins compared to Venus' five. When competing for a title, Serena has the 9-3 record over Venus. There have been nine Williams vs. Williams championship matches in the Grand Slams, including four straight between 2002 and 2003.

Because of the coronavirus pandemic, tennis tournaments had been shut down since March. But, the Top Seed Open -- an outdoor hard court tournament -- became the first WTA Tour event event to be held in the United States since the start of the COVID-19 pandemic. Both Williams sisters decided to play. Lucky for tennis fans, the two have advanced to the second round of the Kentucky-based tournament where they will face each other for the 31st -- and potentially last -- time on Thursday at 1 p.m.

Serena defeated Bernarda Pera in three sets, 4-6, 6-4, 6-1, to advance to the second round while Venus defeated Victoria Azarenka, 6-3, 6-2. The Top Seed Open is the first of WTA's restart to gear up players for the US Open in New York set to begin on Aug. 31. 

Normally, tennis players don't have as long of careers as both Williams sister have had. The sport quickly takes both an emotional and physical toll on tour players. Venus turned 40-years-old this past June and Serena will turn 39 in September. The sisters' second round showdown in Lexington could very well be one of the last times the pair takes the court to play each other. So in honor of Thursday's match, we're going to look back at some of the biggest moments from this special, sister rivalry. 


First pro match

The official beginning of the Williams sisters' rivalry was at the second round of the 1998 Australian Open. Venus won 7–6(4), 6–1. Serena was 16-years-old while Venus was 17 and seeded 16th in the tournament. Venus would go on to lose to Lindsay Davenport 6-1, 5-7, 3-6 in the quarterfinals.

"Serena, I'm sorry I had to take you out," Venus told the NY Times after the win. "Serena hates to lose, and her reputation is she never loses to any one twice."

Serena gets first win

Serena won her first professional match against Venus at the 1999 Grand Slam Cup. It was a three-set win for Serena, 6-1, 3-6, 6-3. The victory came a few weeks after she took home her first Grand Slam singles title at the US Open. Serena was just 18-years-old and defeated Martina Hingis in the US Open championship 6-3, 7-6 (7-4). Serena and Venus would have faced each other in the championship, but Venus fell to Hingins in a three-set semifinal.

Venus beats Serena on grass

The Williams sisters played each other in the 2000 Wimbledon semifinals. It was their first matchup on grass and, while Serena has had the edge over Venus for grass surfaces, Venus got the victory 6–2, 7–6(3). She would go on to win the Wimbledon trophy for her first Grand Slam singles title. 

Back-to-back Grand Slam finals

In 2002, the Williams sisters were dominating the women's game. The pair of young champions met in the 2002 French Open final where Serena took home the win over Venus in a close two-setter, 7-5, 6-3. This was the first final at the French Open ever played by sisters. After the championship, Venus and Serena stood atop the world rankings, sitting at No. 1 and No. 2, respectively. 

Just one month after the French Open final, Serena and Venus met again at the 2002 Wimbledon final. Serena won the match in another close two-setter, 7-6(4), 6-3. The win -- Grand Slam title No. 3 for Serena -- moved her past Venus to take the No. 1 ranking in the world. After both championships, Venus still held the overall head-to-head lead with a 5-4 record.

2008 US Open

Considered to be one of the best matches of the 2008 women's singles season, Serena and Venus played an intense, competitive two-set match at the 2008 US Open quarterfinals. Serena defeated Venus for the win through a pair of tough tiebreaks, 7–6(6), 7–6(7), en route to winning the tournament.  At the end of the 2008 tennis season, their career head-to-head record was tied at 9–9.

First Grand Slam meeting in six years

The Williams sisters would go six years without facing each other on the pro tour. The pair reunited for another matchup in the fourth round of 2015 Wimbledon. It was their first meeting at a Grand Slam since the 2009 Wimbledon final. Serena won the match 6–4, 6–3 and extended her lead in the sisters' head to head record to 15–11.

2017 Australian Open final

After a 14-year absence for Venus in the Australian Open championship, at 37-years-old, she once again made a run. And she faced her younger sister, Serena in the final. Serena would go on to win and take home her seventh Australian Open title and 23rd Grand Slam title overall, defeating Venus 6–4, 6–4. For Serena, the win also brought her to the second-most Grand Slam singles title of all-time, passing Steffi Graf's 22 titles.

2018 US Open third round

This is the sisters' most recent meeting. Two years ago, Serena and Venus faced each other in the third round at the 2018 US Open where Serena advanced 6-1, 6-2.