Adolescents’ own vocational aspirations and those of parents for their adolescent children play significant roles in adolescents’ development. The present study examined how the (in)congruence between adolescents’ vocational aspirations and their parents’ aspirations for them were associated with adolescents’ academic achievement and test anxiety. The study’s sample included 662 parent-adolescent pairs (adolescent Mage = 14.09), and the aspiration and adjustment data were collected at intervals 3 years apart. Using polynomial regression analyses and surface graphs, parent-child aspiration congruence was found to be significantly associated with later academic achievement and test anxiety, but incongruence did not show any significant relationship with either outcome. Such patterns were more prominent among boys (n = 306) than girls and among high socioeconomic status (SES) adolescents (n = 324) than among low SES adolescents. The findings suggest that academic adjustment is more predictable when there is parent-child congruence than when there is incongruence in aspirations.