We employed data from a longitudinal investigation of over 1,000 children who participated in Tulsa’s universal school-based pre-K program in 2005, and path modeling techniques, to examine the contribution of pre-K classroom quality to both kindergarten- and middle-school academic skills. We also examined gender and income-related differences in quality-outcome associations. Both Instructional and Emotional Support in pre-K classrooms, but not Classroom Management, assessed with the Classroom Assessment Scoring System (CLASS), were associated with kindergarten academic skills and, modestly indirectly associated through these immediate impacts, to middle-school test scores. Linear associations were found for Instructional Support whereas nonlinear patterns of association were evident for Emotional Support. Gender and income differences characterized Instructional Support-outcome associations. Results are discussed in terms of implications for improving pre-K quality as one avenue for supporting the ongoing development of academic skills.