When Did Drake Date Serena Williams?

Drake’s new collaboration album with 21 Savage, Her Loss, has raised fans’ eyebrows for many reasons. One of them is that, along with appearing to shade Megan Thee Stallion, the Canadian rapper also seems to take a dig at Serena Williams’ husband — Reddit co-founder Alexis Ohanian. “Sidebar, Serena, your husband a groupie / He claim we don’t got a problem but / No, boo, it is, like you comin’ for sushi / We might pop up on ’em at will like Suzuki,” he raps on the solo song, “Middle Of The Ocean.”

“The reason I stay winning is because I’m relentless about being the best at whatever I do—including being the best groupie for my wife & daughter,” Ohanian seemed to coyly respond to Drake’s line on Twitter today.

Many new fans might be wondering: did Drake and Serena date? And if so, when? The answer is… they might have. In 2011, he was first recorded attending her matches, and even hinted at their relationship on Twitter. “@SerenaWilliams I cannot wait to put it on you and make you sweat……. during our match this weekend,” Drake posted, according to Capital Xtra.

From there, he also namedropped the tennis legend for the first time. In TK, on his song “Worst Behaviour,” Drake notes, “I’m with my whole set / Tennis matches at the crib / I swear I could beat Serena when she playin’ with her left.” Drake would go on to exchange disses with Williams’ ex, rapper Common. “For me, I think it was an emotional thing,” Common eventually shared in an interview. “Unfortunately the war might have been over a girl, even though at the time I never said that.”

Drake continued to be spotted at her tennis games over the years. There were two alleged videos of them making out that circulated online — once in a Cincinnati restaurant and the other leaving a spot to get into a car. They even left together at the US Open semi-finals in 2015.

Yet, things clearly didn’t work out. Williams married Ohanian in 2017, and the couple welcomed their first child, Alexis Olympia, that same year.

Drake’s last known interaction, prior to this diss, was attending Wimbledon in 2018 — where Williams played.

Some artists covered here are Warner Music artists. Uproxx is an independent subsidiary of Warner Music Group.