5 Times Drake Took Shots At Serena Williams: From Sneaky Lyrics To The Latest Instagram 'Upgrade' Diss

The relationship between global superstar Drake and tennis legend Serena Williams has always been a source of intense media fascination, a dynamic fueled by the rapper's tendency to reference—and sometimes subtly diss—the athlete in his music and on social media. As of late 2025, the conversation has reignited, moving beyond old song lyrics to a shocking new social media incident where Drake appeared to co-sign a comment that called a fellow rapper a "Serena Williams upgrade," proving that the decade-long tension between the two celebrities is far from over. The history of their connection, which spanned an on-again, off-again romance between 2011 and 2015, is littered with lyrical jabs and public appearances that have kept fans guessing about their true feelings for one another. To fully understand the current drama, one must trace the timeline of Drake's most notable comments, from playful boasts to outright shade.

Serena Williams: A Complete Profile

Before diving into the controversial comments, it is essential to appreciate the sheer magnitude of Serena Williams' career, which makes any public slight against her a major headline. Born in Saginaw, Michigan, Williams rose from the public courts of Compton, California, to become arguably the greatest female tennis player of all time.

• Full Name: Serena Jameka Williams
• Born: September 26, 1981 (Age 44 as of December 2025)
• Birthplace: Saginaw, Michigan, U.S.
• Height: 5 ft 9 in (175 cm)
• Career Status: Retired (Played final professional match at the 2022 US Open)
• Key Achievements:
  • 23 Grand Slam Singles Titles (Open Era record)
  • 14 Grand Slam Doubles Titles (with sister Venus Williams)
  • Only player, male or female, to complete three career Golden Slams.
  • Held World No. 1 ranking for 319 total weeks.
  • Career Prize Money: Over $94 million.
• Husband: Alexis Ohanian (Co-founder of Reddit)
• Children: Alexis Olympia Ohanian Jr. and Adira River Ohanian

The Evolution of Drake’s Comments: From Playful Boast to Public Diss

Drake’s comments about Serena Williams have changed significantly over the years, mirroring the complexity of their private relationship. What started as a flirtatious boast in a song evolved into more pointed, and sometimes shady, references as their paths diverged.

1. The "Worst Behavior" Boast (2013)

The first widely recognized reference came on Drake's 2013 album, Nothing Was the Same, on the track "Worst Behavior." This lyric is often cited as the beginning of their public narrative.

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The Quote: "I'm with my whole set, tennis matches at the crib / I swear I could beat Serena when she playin' with her left."

The Context: This line was a classic Drake boast, implying a level of intimacy and familiarity with the tennis champion—suggesting he was close enough to her to watch her practice and confident enough to think he could beat her even when she was playing non-dominant hand. At the time, they were rumored to be dating on-and-off.

2. The Meek Mill Diss Track Hint (2015)

In 2015, Drake released the famous diss track "Charged Up" aimed at Meek Mill, during which he casually suggested Williams was involved in the song’s creation.

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The Quote: Drake reportedly suggested Williams helped him finish the track.

The Context: This reference came when Drake and Williams were photographed together, fueling dating rumors. Including her name in a major hip-hop beef track was seen as a bold move, linking the tennis world to his music career and asserting their close bond in a high-stakes public moment.

3. The "Middle Of The Ocean" Jab (2022)

Years after their relationship ended and Williams married Reddit co-founder Alexis Ohanian, Drake returned to the topic on his 2022 album with 21 Savage, Her Loss. This time, the reference was less playful and more pointed.

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The Quote: On the track "Middle Of The Ocean," Drake referenced Williams by name while taking a jab.

The Context: This line was interpreted by many as a subtle jab at her marriage or her current life, suggesting a lingering feeling about their past. The track itself is known for Drake's boastful and sometimes controversial lyrics, and Williams' name was used to underscore a point about his own status and relationships.

4. The Instagram "Serena Williams Upgrade" Diss (Latest Incident)

The most recent and controversial incident occurred on Instagram, bringing the decade-long tension back into the spotlight in late 2024/early 2025. This time, Drake didn't say the words himself, but his action spoke volumes.

The Action: Drake posted a photo set, captioning it, "I said tennis lesson she said where's the bracelet or the necklace.” A commenter then wrote, "Serena Williams upgrade," referring to the rapper Sexyy Red, who was featured in the photos. Drake subsequently "liked" the comment.

The Context: Liking the comment was widely interpreted as Drake co-signing a diss that positioned Sexyy Red as a superior romantic partner to the tennis icon. This move sparked significant controversy across social media, with fans and critics calling it "shady" and disrespectful to the mother of two and global sports figure.

5. Serena's Subtle Response to the Drama (2025)

While Serena Williams rarely addresses Drake directly, she offered a subtle, yet firm, statement that seemed to distance herself from the constant media speculation surrounding their past.

The Quote: In a national TV interview, Williams reiterated that her Super Bowl cameo "was not about Drake."

The Context: This comment, reported in May 2025, came after her appearance at the Super Bowl halftime show led to renewed discussion about her relationship with the rapper. Her statement served as a clear message that she has moved past the drama and that her career and public appearances are not dictated by their history.

The history of Drake's comments about Serena Williams is a perfect encapsulation of how modern celebrity relationships play out in the public eye. From the playful flirtations in his early career to the more pointed social media actions of today, the rapper has continuously used the tennis legend as a reference point in his narrative, ensuring that the saga of their brief but impactful romance continues to generate headlines years later.