The Toronto Maple Leafs found an unlikely source repping them on Monday night. Sabrina Carpenter, the former Disney star turned global pop icon, was seen repping a pair of Leafs-branded custom silver boots on Monday night. But Carpenter had an extended stay in the city while working on the 2019 film Work It. Interestingly, it’s not the first time Carpenter has worn Leafs gear on stage — or even on this tour. Carpenter rocked a Leafs jersey on stage for a September 2024 show, with the pictures from that night still going viral every few months.