Fans on social media have shared recordings from recent stops of Drake's It's A Blur Tour, which he is headlining with fellow rapper 21 Savage.
Footage from Chicago, New York and Montreal shows a woman's head that looks strikingly like Wintour's - complete with the fashion editor's signature bob and sunglasses. The woman's skin is extremely wrinkled and her villainous laugh appears to expose rotten teeth.
Neither Drake or 21 Savage have explicitly said the figure featured in their recent performances is Wintour, but fans have pointed out the similarity, captioning TikTok videos with comments like "Drake so petty for putting Anne (sic) Wintour up here like this" and "Drake vs Anna Wintour".
In February, Drake and 21 Savage settled a lawsuit after using a fake Vogue cover to promote their 2022 album, Her Loss.
According to reports, Vogue's parent company Condé Nast asked for $4m (£3.3m).
Condé Nast reportedly claimed the rappers' promo campaign was built "entirely" on the unauthorised use of Vogue trademarks and false representations.
Reuters news agency said it had seen a memo sent to employees in February telling them the rappers had agreed to pay the magazine.
Drake and 21 Savage's It's A Blur tour is currently making its way through the US and Canada.
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