While much research examines education spending at the school district level in the United States, few studies analyze resource allocation to schools within districts and its relationship with educational outcomes. This study focuses on the relationship between “progressivity,” which is the extent to which a district weighs funding allocation based on schools’ poverty rates, and math and English test scores. Using school-level per pupil spending data from Massachusetts, I find that progressivity varies markedly across school districts: 96 of 220 school districts (44%) allocate more money to schools with less economically disadvantaged students. Regression results indicate that per pupil spending is positively associated with improvements in math achievement in progressive school districts and with English achievement in all school districts. These findings suggest that state policymakers should consider setting minimum spending requirements at the school level to offset current resource allocation decisions by districts. At the same time, these results also suggest that these improvements in achievement might be driven by improvements by non-economically disadvantaged students, implying that financial support to schools with disadvantaged students do not necessarily benefit those students. This study provides a steppingstone for future research on the effects of spending at the school level on student achievement.