The Full History: 5 Times Drake Has Publicly Spoken About Or Shaded Serena Williams

The dynamic between global superstar Drake and tennis legend Serena Williams has been a source of intense public fascination for over a decade. What began as a rumored romance in the early 2010s has evolved into a complex narrative of musical references, subtle disses, and public shade. As of late 2024 and early 2025, the tension has flared up again, with Drake's social media activity and Serena's public responses keeping the long-standing, unconfirmed relationship drama in the headlines. The question of "what did Drake say about Serena Williams" is not a simple one, as his comments span from supportive attendance at her matches to making jabs at her husband in a song. This deep dive explores the full timeline of Drake’s public statements, lyrics, and actions concerning the 23-time Grand Slam champion, revealing the layers of their complicated history.

The A-List Biographies: Drake and Serena Williams

To understand the context of their public interactions, it is crucial to know the monumental stature of both figures.

Aubrey "Drake" Graham

• Full Name: Aubrey Drake Graham
• Born: October 24, 1986 (Age 39 as of late 2025)
• Place of Birth: Toronto, Ontario, Canada
• Occupation: Rapper, Singer, Songwriter, Actor, Record Producer, Entrepreneur
• Notable Achievements: Multiple Grammy Awards, co-founder of OVO Sound, holds numerous streaming and chart records, one of the best-selling music artists of all time.
• Key Albums Mentioned: Nothing Was the Same, Views, Her Loss

Serena Jameka Williams

• Full Name: Serena Jameka Williams
• Born: September 26, 1981 (Age 44 as of late 2025)
• Place of Birth: Saginaw, Michigan, U.S.
• Occupation: Professional Tennis Player (Retired), Entrepreneur, Investor
• Notable Achievements: 23 Grand Slam singles titles (Open Era record), 4 Olympic gold medals, former World No. 1 in singles and doubles, widely regarded as one of the greatest athletes of all time.
• Spouse: Alexis Ohanian (m. 2017)
• Child: Alexis Olympia Ohanian Jr.

The Relationship Timeline: From Rumors to Public Support (2011–2015)

The relationship between Drake and Serena Williams was never officially confirmed by either party, but their on-again, off-again romance was one of the most talked-about celebrity pairings of the decade. They were first linked around 2011.

The rumors intensified significantly in 2015 when Drake was frequently spotted in Serena’s box at major tennis tournaments, including the Rogers Cup and the US Open. This public support led to widespread speculation that they were seriously dating.

• The Surprise Vegas Wedding And Shared Grief 5 Shocking Details Of John Schneider And Dee Dee Sorvinos Whirlwind Romance Ohirf

The most concrete evidence of their romance came in August 2015, when TMZ published photos of the two making out at a restaurant in Cincinnati. Despite this, the relationship reportedly "fizzled out" by the end of that year, just before Serena began dating her future husband, Reddit co-founder Alexis Ohanian.

The 5 Key Times Drake Referenced Serena Williams Publicly

Drake’s references to Serena Williams have been consistent throughout his career, often serving as a barometer for his feelings at the time. These are the most significant instances:

1. The Competitive Lyric: "Worst Behaviour" (2013)

One of Drake’s earliest and most memorable references to Serena came in the song "Worst Behaviour" from his 2013 album, Nothing Was the Same. The line was a boast about his lifestyle, but also a direct, competitive name-drop:

• The Untouchable Privacy 7 Secrets Of Rachel Mcadams And Jamie Lindens Life Beyond The Red Carpet E820e

"I'm with my whole set, tennis matches at the crib / I swear I could beat Serena."

While seemingly a playful boast, this lyric established that Serena was a fixture in his private life and a point of reference in his music, long before the 2015 public sightings.

2. The Breakup Song: "Too Good" (2016)

Years later, Drake confirmed that the hit song "Too Good," featuring Rihanna, was inspired by his relationship with Serena Williams. The song, which explores the breakdown of a relationship where both parties felt they were "too good" for the other's treatment, is widely interpreted as his musical commentary on their split.

• The Chilling True Story 5 Key Facts About Richard Evonitz The Serial Killer Who Kidnapped Kara Robinson Chamberlain Xpjje

This confirmation was significant because it moved the narrative from mere speculation to an acknowledged, albeit one-sided, account of their romance and its end.

3. The Jab at Her Husband: "Middle of the Ocean" (2022)

In 2022, Drake appeared to reignite the drama in his track "Middle of the Ocean" from the album Her Loss. By this time, Serena was married to Alexis Ohanian and had a daughter. Drake took a direct shot at Ohanian, suggesting he was not on Drake's level:

"Sidebar, Serena, your husband a groupie / He love my music, he CD comin' to me."

This lyric was a clear attempt to diminish Ohanian, implying that the tech mogul was merely a fan of Drake's, positioning himself as the superior romantic option, years after the fact. It was one of Drake's most direct and controversial comments on Serena's personal life.

4. The Shady Instagram Like (Late 2024/Early 2025)

In a more recent, subtle act of shade, Drake sparked fresh drama with a seemingly innocent social media post. After posting a picture with rapper Sexyy Red, he captioned it with a lyric about giving tennis lessons. A commenter responded, calling Sexyy Red a "Serena Williams upgrade."

Drake, known for his calculated social media moves, quietly liked the comment. This act was immediately interpreted by fans and media outlets as a low-key, yet intentional, diss aimed at his ex-girlfriend, suggesting he was endorsing the comparison and the idea of an "upgrade."

5. Serena's Response: Dancing to the Diss Track (2024 ESPY Awards)

While Serena Williams has almost never publicly engaged with Drake's comments or lyrics, she delivered a powerful, non-verbal response in 2024. While hosting the ESPY Awards, she was seen dancing to Kendrick Lamar's "Not Like Us"—a song that is a direct and brutal diss track aimed at Drake during their high-profile feud.

By publicly celebrating a track designed to mock and criticize her ex-boyfriend, Serena effectively took a side in the rap beef and sent a clear message that she was not only aware of the drama but was actively trolling Drake on a major televised stage. This act served as her most recent and definitive public statement on their complex history.

Topical Entities and LSI Keywords

The narrative surrounding Drake and Serena Williams is rich with interconnected entities that contribute to the story's topical authority:

• Alexis Ohanian (Serena's Husband)
• Kendrick Lamar (Rapper and Drake's Feud Rival)
• Sexyy Red (Rapper in recent Instagram post)
• Rihanna (Collaborator on "Too Good")
• "Worst Behaviour" (Song Title)
• "Too Good" (Song Title)
• "Middle of the Ocean" (Song Title)
• "Not Like Us" (Kendrick Lamar Diss Track)
• OVO Sound (Drake’s Record Label)
• Reddit (Alexis Ohanian’s Company)
• US Open (Tennis Tournament)
• Rogers Cup (Tennis Tournament)
• The ESPY Awards (2024 Event)
• Grand Slam Titles (Serena's Achievement)
• Dating Rumors (Core Topic)
• Celebrity Feuds (Context)

The complex relationship between Drake and Serena Williams continues to generate headlines because of the public's enduring curiosity about their past. Drake's tendency to weave his personal life into his music and social media ensures that every subtle comment, lyric, or even a simple Instagram "like" will be scrutinized, keeping the conversation about "what did Drake say about Serena Williams" alive and updated with fresh drama.