Although a positive association between students' satisfaction with academic achievement and psychological well-being has been well-documented, less is known about whether this association is moderated by parental satisfaction with children's academic achievement. The objective of this study is to address this knowledge gap. This study utilized data from Wave 1 (2018) to Wave 3 (2020) of the Korean Children and Youth Panel Survey 2018 (KCYPS 2018), comprising a sample of 3,871 students from Grades 4 and 7. Children's and parents' satisfaction with academic achievement were considered as key independent variables. Psychological outcomes included depressive symptoms, life satisfaction, and self-esteem. Fixed effects models were estimated to account for unobserved time-invariant confounding factors. Children's satisfaction with academic achievement was significantly associated with a decrease in depressive symptoms ( b = −0.398) and an increase in life satisfaction ( b = 0.593) and self-esteem ( b = 0.643). The interaction model revealed that the association between students' satisfaction with academic achievement and psychological outcomes is strengthened when parental satisfaction is higher. Efforts to foster a positive attitude toward academic achievement in both students and parents can enhance adolescents' psychological well-being. Interactive communication between parents and children regarding academic achievement will be required.