The primary goal of this study was to longitudinally evaluate the homework assignment completion patterns of middle school age adolescents with ADHD, their associations with academic performance, and malleable predictors of homework assignment completion. Analyses were conducted on a sample of 104 middle school students comprehensively diagnosed with ADHD and followed for 18 months. Multiple teachers for each student provided information about the percentage of homework assignments turned in at five separate timepoints and school grades were collected quarterly. Results showed that agreement between teachers with respect to students’ assignment completion was high, with an intraclass correlation of .879 at baseline. Students with ADHD were turning in an average of 12% fewer assignments each academic quarter in comparison to teacher-reported classroom averages. Regression analyses revealed a robust association between the percentage of assignments turned in at baseline and school grades 18 months later, even after controlling for baseline grades, achievement (reading and math), intelligence, family income, and race. Cross-lag analyses demonstrated that the association between assignment completion and grades was reciprocal, with assignment completion negatively impacting grades and low grades in turn being associated with decreased future homework completion. Parent ratings of homework materials management abilities at baseline significantly predicted the percentage of assignments turned in as reported by teachers 18 months later. These findings demonstrate that homework assignment completion problems are persistent across time and an important intervention target for adolescents with ADHD.