Striking statistically significant differences were noted across school ranking conditions in terms of professional teacher preparation, organizational health variables, school leadership characteristics, academic emphasis, and resource support. The general conclusion of this study is that a strong correlation exists between structural equity issues in middle schools and academic achievement. A large representative sample of middle schools was targeted for systematic study. The schools were categorized into three clusters (high, middle, and low performing schools). Participants were asked to complete an adapted version of the Hoy and Sabo (1998) OHI-RM (Organizational Health Inventory- Revised Middle) instrument. Statistically significant differences were documented across the three categories. The findings provide support for the view that structural instructional problems may create educational inequities that lead to academic achievement disparities.