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The present study examines the relationships between high school students’ academic achievement and five types of parental involvement—school-based involvement, homework assistance, intellectual enrichment, parent-child educational discussions, and parental expectations. This study also explores whether the relationship between parental involvement and students’ academic achievement varies by parent sex. We used a sample of 5063 adolescents from the High School Longitudinal Study of 2009. By using both hierarchical regression and moderation analyses, we found that school-based involvement and homework assistance were the two strongest predictors of GPA. However, homework assistance yielded a negative association with achievement. Results also indicated that fathers’ involvement had a stronger relationship with students’ GPAs than mothers, even though fathers reported less involvement in conversations.