This instrumental case study explored the contextual knowledge urban music educators hold about their particular learners and the school, community, and broader cultural contexts in which they are situated. The two urban choral music educators who participated in the study represented unusual cases in that they were employed by a children's choir organisation to teach in multiple demographically contrasting classrooms each week. The study explored a week in these teachers' lives, affording a view of individual teachers' knowledge of varied urban contexts. While adjustments could be discerned in teachers' pedagogical responses to each classroom based on pedagogical context knowledge, consistencies in teacher's practice across settings illuminated facets of their personal practical knowledge. Participants enacted their specialised knowledge of the urban context through culturally relevant and anti-racist pedagogy. Implications for music teacher education are discussed based on the findings.