The first time Serena Williams (37) faced off against Maria Sharapova (32) was in 2004 at the Miami Masters. Williams would win in straight sets 6-4, and 6-3. Across both of their long careers, not much has changed in the winning category as Williams holds a 19-2 advantage.
On August 26, 2019, Sharapova has a chance to make that 19-3.
The 37-year-old eighth-seed drew the unseeded 32-year-old in the first round of the U.S. Open during a ceremony on August 22. Williams shows no pity when it comes to Sharapova. She's taken her down one very surface, even blue clay that was introduced as a novelty for one week only in Madrid. The only thing Sharapova has going for her this time is that they've never traded serves at the U.S. Open.
Dating back to 2005, Williams has been victorious in 18 consecutive matches against her upcoming opponent. The only reason why this star-studded match is possible is due to Sharapova's recent injury woes. Missing most of the season dropped her ranking to 87.
Not only do the two have a history on the court, but the drama is even richer off it. In a 2013 Rolling Stone profile, Williams seemed to take jabs at her peer.
"She begins every interview with 'I'm so happy. I'm so lucky' – it's so boring," says Serena. "She's still not going to be invited to the cool parties. And, hey, if she wants to be with the guy with a black heart, go for it." (she's talking about Sharapova, who was dating Grigor Dimitrov, one of Serena's rumored exes.) We'll see how things go this time around, maybe the underdog comes out on top.