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This paper presents a case study of an anti-oppressive knowledge sharing initiative from one Toronto secondary school focused on critical global citizenship. Funded by a 2021 grant from the Social Sciences and Humanities Research Council of Canada (SSHRC) and the Toronto District School Board, this research project provides support for secondary school educators in de-streamed classrooms to develop anti-oppressive pedagogical praxis using a tool called HEADSUP. This project was framed by critical global citizenship education, critical race theory, and intersectionality theory. Findings from the teacher interviews suggest that while the tool was helpful for advancing anti-oppressive education, persistent challenges due to the COVID-19 context as well as limited knowledge of anti-oppressive pedagogies by educators remained barriers.