Drake has found himself back in the conversation with tennis fans and hip-hop followers alike after appearing to take another swipe at Serena Williams in a new tennis-inspired photoshoot with rapper Sexyy Red.
What began as a playful set of court-side images quickly shifted into controversy when the Toronto star endorsed a comment that compared Sexyy Red favorably to the 23-time Grand Slam champion, breathing new life into a feud many assumed had faded.
Drake’s History With Serena Williams Makes This Moment Explosive
The moment instantly drew attention because of Drake’s long and complicated history with Williams. The pair dated on and off during the early 2010s and were frequently spotted together, including a 2015 dinner outing in Cincinnati.
Their rumored split later surfaced in Drake’s music, most notably in his 2016 track “Too Good,” where he lamented feeling underappreciated, rapping, “I’m too good to you/ I’m way too good to you/ You take my love for granted/ I just don’t understand it.”
This time, the drama erupted after Drake posted a series of tennis-themed photos with Sexyy Red on Instagram, captioned, “I said tennis lesson she said where’s the bracelet or the necklace.”
Fans flooded the comments, but one remark in particular became the center of attention. A user wrote, “Serena Williams upgrade,” adding several fire emojis. Instead of scrolling past the dig, Drake liked the comment.
A Look Back at Drake’s Turbulent History With Williams
Fans took the seemingly small action as a pointed jab at his former partner, and within hours, the endorsement resurfaced old grievances tied to their past drama. The incident also reawakened memories of Drake’s 2022 lyric on “Middle of the Ocean,” where he called Williams’ husband Alexis Ohanian “a groupie” and insisted there was tension between them.
Kendrick Lamar later backed Williams during his own feud with Drake, rapping, “From Alondra down to Central, n**ga better not speak on Serena,” in his track “Not Like Us.” Williams publicly echoed that stance while hosting the 2024 ESPYs, noting that it was unwise for anyone to keep a dispute going with Lamar.
MORE: Serena Williams Makes Her Position Clear on Women Being ‘Not Taught’ To Celebrate Milestones
“And if I’ve learned anything this year, not a single one of us, not even me, should ever pick a fight with Kendrick Lamar. He will make your hometown not like you,” she said. “The next time Drake sits courtside at a Raptors game, they’re gonna Forrest Gump him, seats taken.”
She later expressed her appreciation for Lamar’s song and even joined him for a brief “Crip Walk” cameo during the Super Bowl Halftime Show as he performed “Not Like Us,” which many labeled a diss aimed squarely at Drake.
Although she insisted the dance was not meant as shade and harbored no resentment toward her ex, the rapper’s latest like has reopened speculation about unresolved emotions on his end.
