This study sheds light on how large-scale school fundraising efforts differ according to locations in unequal and segregated cities, putting a greater burden on schools in under-resourced areas. In particular, we compare the large-scale fundraising campaigns of two high schools in contrastingly unequal urban neighbourhoods in one of Canada's prairie provinces. We apply critical space analysis to compare their respective communities, actors, strategies, discourses as well as time. Our comparison indicates that unequal levels of community wealth led to inherently uneven processes, with a greater and more prolonged fundraising burden on schools in low-income and under-resourced areas. We conclude by discussing how these large-scale school fundraising inequities constitute new structural inequities, symbolic domination, and spatial violence.