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Drake reignites Serena Williams feud with pointed dig during raunchy photoshoot with Sexyy Red

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Drake has seemingly reignited his long-running feud with ex-girlfriend Serena Williams after making a pointed dig at the tennis star on his Instagram. 

On Monday, the Canadian rapper – who previously dated Williams from 2011 to 2015 – took to the social media platform share a picture alongside fellow artist ‘Sexyy Red’. 

The duo posed for a series of tennis-themed photos, with Drake captioning it: ‘I said tennis lesson she said where’s the bracelet or the necklace’.

However, eagle-eyed fans were quick to note a subtle dig from the ‘Hotling Bling’ rapper, when they headed down into the comment section. 

They noticed that Drake had liked one comment from a user, which read: ‘Serena Williams upgrade [fire emojis]’.

It marks just the latest subtle dig between Drake and Williams, who have been consistently throwing shade at one another in recent years. 

Serena Williams

Drake

Drake has seemingly reignited his feud with ex-girlfriend Serena Williams with a post online 

The Canadian rapper shared a picture with fellow artist 'Sexyy Red' on Monday afternoon

The Canadian rapper shared a picture with fellow artist ‘Sexyy Red’ on Monday afternoon

One user commented: 'Serena Williams upgrade' which the 'Hotline Bling' rapper liked

One user commented: ‘Serena Williams upgrade’ which the ‘Hotline Bling’ rapper liked

Perhaps the most notable incident was when tennis star Williams made a surprise cameo in Kendrick Lamar’s 2025 Super Bowl performance earlier this year. 

Williams showed up and started dancing while Lamar was performing his song ‘Not Like Us’ – a diss track from his beef with Canadian rapper Drake.

She wasn’t seen up close, but a tweet from the tennis icon after the game showed her in the exact same outfit as the performance.

‘Let’s go Super Bowl halftime??! I died a little!,’ the star tweeted

The sight of Williams c-walking on a stage as big as this sent social media into hysterics. 

In the midst of their Drake’s beef with Lamar, Serena delivered a jab of her own at the 2024 ESPYS, which she hosted: ‘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.’

She added: ‘He will make your hometown not like you. The next time Drake sits courtside at a Raptors game, they’re gonna Forrest Gump him, “seat’s taken”.’

Shortly after Williams’ shock appearance at the Super Bowl, Drake seemingly made a subtle dig at the 23-time Grand Slam winner on his private Instagram account. 

Drake and the tennis icon were first romantically linked back in 2011 - and Serena shocked fans when she was spotted Crip walking to a Drake diss song during a Kendrick Lamar performance

Drake and the tennis icon were first romantically linked back in 2011 – and Serena shocked fans when she was spotted Crip walking to a Drake diss song during a Kendrick Lamar performance

In response, the Canadian-born rapper took a thinly veiled dig at Williams when he posted a photo of himself with her former agent, Jill Smoller

In response, the Canadian-born rapper took a thinly veiled dig at Williams when he posted a photo of himself with her former agent, Jill Smoller

In response, the Canadian-born rapper took a thinly veiled dig at Williams, 43, when he posted a photo of himself with her former agent, Jill Smoller. 

The image was taken in 2015 when he attended Wimbledon to watch Serena compete in a match. 

Drake – whose full name is Aubrey Drake Graham – opted to not add a caption to the picture, but left the comment section open to allow social media users to offer their own thoughts. 

Drake and Williams were first romantically linked in 2011 and four years later in 2015, the pair were spotted together on various occasions – such as kissing at a Cincinnati restaurant. 

However, the two stars went their separate ways and the following year in 2016 – he dropped the track Too Good where he appeared to reference the tennis player. 

The lyrics in the chorus are: ‘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.’

Williams later tied the knot with Alex Ohanian in 2017 and Drake seemingly reference to her husband in his 2022 song titled Middle of the Ocean.

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