Variations in pubertal timing and tempo have relevance to psychosocial development. Accounting for pubertal timing, tempo, and psychosocial development simultaneously in a model remains challenging. This study aimed to document the typology of pubertal development in a cohort of Taiwanese adolescent boys and then to examine how the associations between psychosocial variables across time vary by the patterns of pubertal development. A group of adolescent boys (n = 1,368) reported pubertal signs and psychosocial variables for 3 years since seventh grade. The growth mixture model revealed three major classes of pubertal transition: average pubertal growth, late-onset with rapid catch-up, and late-onset with slow catch-up. In a cross-lagged panel model, the multigroup analysis found the regression coefficients mostly invariant across all three classes, except those between deviant behavior and subsequent changes in depressive symptoms that were significantly positive only in the late-onset with slow catch-up group. Adolescent boys in this group were estimated to have the highest marginal level of depressive symptoms and deviant behavior in ninth grade among the three classes. Our study highlights the heterogeneity in boys’ pubertal development and the role of the pubertal development pattern in their psychosocial development.