Drake, Serena Williams Cole Burston/Getty Images;Kevin Mazur/Getty Images for Roc Nation
Nearly 10 years after Serena Williams’ rumored romance with Drake, the tennis pro turned heads — and brought attention back to their alleged relationship — by seemingly dissing the rapper during the 2025 Super Bowl halftime show.
Williams, 43, raised eyebrows on Sunday, February 9, when she danced on a grave as part of Kendrick Lamar’s halftime show. While her cameo was surprising, the fact that she joined the musician for “Not Like Us,” a diss track directed at Drake, 38, was even more shocking.
To understand why, Us Weekly is taking it all the way back to the summer of 2015 — and breaking down the sorted history between Williams and Drake.
Drake became a fixture at Williams’ tennis matches that summer, starting in England during Wimbledon, from June through early July.
Serena Williams shocked the audience when she made a surprise cameo at the 2025 Super Bowl halftime show with Kendrick Lamar. “Let’s go Super Bowl halftime??! I died a little!” Williams, 43, wrote via X on Sunday, February 9, alongside a video of her dancing while rocking her performance outfit, which included a blue pleated […]
The Degrassi: The Next Generation alum was spotted sitting next to Serena’s sister, Venus Williams, during her quarterfinal win over Victoria Azarenka in July 2015, according to reporter Ben Rothenberg via Bounces.
After her semifinal win against Maria Sharapova, a reporter asked Serena whether Drake was her “lucky mascot,” according to the Associated Press, which reported that Drake was in attendance for the press conference and laughed before covering his face.
Serena, meanwhile, reportedly told the press, “We’ve been friends for, like, so many years. Just like family.”
Although they played coy about their connection, Drake was part of Serena’s player box when she won her sixth Wimbledon title later that month. He continued to pop up at her tournaments, appearing at Toronto’s Rogers Cup in August 2015.
It wasn’t until Drake attended the Women’s Tennis Association tournament in Ohio that August that fans started speculating that they could be more than just friends. Drake and Serena were spotted kissing at a local restaurant after the event, which fueled romance rumors.
Edward Berthelot/Getty Images Venus Williams is proving she’s her sister’s No. 1 fan after Serena Williams made a surprise appearance at the 2025 Super Bowl Halftime Show. “Lil sis killing it,” Venus, 44, wrote via her Instagram Story on Monday, February 10, reposting Serena’s video from the performance. Venus also commented on Serena’s Sunday, February […]
Serena, for her part, had already met her now-husband, Alexis Ohanian, in May 2015 while they were staying at the same hotel in Rome.
While Serena’s romance with Ohanian, now 41, continued to grow outside the spotlight, her status with Drake remained a topic of conversation.
In fact, when Serena lost her bid for the Grand Slam in September 2015, the internet blamed Drake. (Drake was in attendance when Serena played in the U.S. Open and lost, barring her from a Grand Slam appearance.)
“I blame Drake for this,” one user wrote via X at the time. A second user tweeted, “Drake jinxed Serena, man.”
The following month, Serena’s rep denied that she and Drake were romantically involved. “They are simply longtime friends,” the rep told People in October 2015.
Serena quieted the rumors herself in December 2015 when she brought Ohanian as her plus one to accept the award for 2015’s Sports Illustrated Sportsperson of the Year.
The tennis legend got engaged to Ohanian in December 2016 and tied the knot in New Orleans in November 2017. The couple share two daughters, Alexis Olympia and Adira.
While Drake became a father himself in October 2017 when he welcomed son Adonis with ex Sophie Brussaux, his rumored feelings for Serena have remained a topic in his music.
In his 2022 song “Middle of the Ocean,” Drake slammed Ohanian’s relationship with Serena. “Sidebar, Serena, your husband a groupie / He claim we don’t got a problem but, no, boo, it is like you comin’ for sushi,” he rapped.
Gregory Shamus/Getty Images Kendrick Lamar brought his now Grammy-winning trolling of Drake to the biggest stage imaginable at the 2025 Super Bowl halftime show at the Caesars Superdome in New Orleans. After months of speculation about his setlist, Lamar, 37, included “Not Like Us” in his performance, meaning that more than 73,000 fans got to […]
Ohanian clapped back at the lyrics via X, writing in November 2022, “The reason I stay winning is because I’m relentless about being the absolute best at whatever I do — including being the best groupie for my wife & daughter.”
The Reddit founder added: “In @serenawilliams I found a partner I knew I would never outgrow, who would always motivate me to be Greater.”
Nearly two years later, Drake brought his and Serena’s rumored fling back into the spotlight when his 100 Gigs archival videos captured footage about his 2016 hit “Too Good.”
Drake name dropped Serena while speaking with his mom about the song, telling her in the throwback video, “I get heavy on a couple joints, but this is more about me and Serena.”
“I gather!” his mom, Sandi Graham, said in the clip which was published to 100 Gigs in August 2024.
In the song, Drake sings about a one-sided romance, which he hinted was the situation between him and Serena. “It’s funny because when I make songs about women, I also make songs for them,” the rapper said at the time. “So, I know what kind of song to make. If I’m gonna talk about them, I’ll at least do them the justice of making them a song that they’ll like.”
Drake alleged, “I know Serena very well, and I know that she’ll hear it loud and clear but not hate me for it because it’s lighthearted.”
Graham then asked Drake, “And she is seeing someone else?” hinting she knew about their rumored romance. “I don’t know, mom,” Drake confessed.
Flash forward to February, when Serena seemed to clap back at Drake’s jabs over the years while siding with Lamar at the Super Bowl. (Lamar and Drake have been in an ongoing feud since 2013.)
“Let’s go Super Bowl halftime??! I died a little!” Serena wrote via X after she took the field to dance to “Not Like Us.”
The song itself has ties to both Drake and Serena, as Lamar tells his nemesis in the track (which is widely thought to be Drake) that he “better not speak on Serena.”
Serena previously commented on Lamar’s song while hosting the ESPY Awards in July 2024. “If I’ve learned anything this year, it’s that none of us, not a single one of us, not even me, should ever pick a fight with Kendrick Lamar,” Serena teased at the time. “He will make your hometown not like you. The next time Drake sits courtside at a Raptors game, they’re going to Forrest Gump him. Seats taken.”
