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This study aimed to examine the effect of prekindergarten (pre-K) to second-grade classroom quality on students’ kindergarten (K)-, first-, and second-grade academic achievements. Data were analyzed with multilevel structural equation models (SEMs) by accounting for the dependency among observations that were cross-classified with multiple classrooms over four grade-levels. Prior to examining the effect of classroom quality, within-school-year and carryover effects from early years’ classrooms were also explained. Analysis results showed that the effect of overall classroom quality on student outcomes was only demonstrated for the first-grade classrooms on reading scores within the same school year. As per domain-specific quality measures, the effect of classroom organization was consistently positive and significant on multi-year outcomes at different grade levels.