This longitudinal study of affluent suburban youth (N = 319) tracked from 6th to 12th grade is parsed into two segments examining prospective associations concerning emotional-behavioral difficulties and academic achievement. In Part 1 of the investigation, markers of emotional-behavioral difficulty were used to cluster participants during 6th grade. Generalized estimating equations were then used to document between-cluster differences in academic competence from 6th to 12th grade. In Part 2 of the study, indicators of academic competence were used to cluster the same students during 6th grade, and generalized estimating equations were used to document between-cluster differences in emotional-behavioral difficulty from 6th to 12th grade. The results from Part 1 indicated that patterns of emotional-behavioral difficulty during 6th grade were concurrently associated with poorer grades and classroom adjustment with some group differences in the rate of change in classroom adjustment over time. In Part 2, patterns of academic competence during 6th grade were concurrently associated with less emotional-behavioral difficulty and some group differences in the rate of change in specific forms of emotional-behavioral difficulty over time. These results suggest that the youth sampled appeared relatively well adjusted and any emotional-behavioral-achievement difficulty that was evident at the start of middle school was sustained through the end of high school.