Parental involvement in adolescents’ learning has been linked to high academic achievement, yet few studies have examined its reverse relationship at the same time and the potential mechanisms that underly these associations. To address this research gap, this study investigated the reciprocal relationship between parental involvement and academic achievement as well as the mediating role of adolescents’ academic engagement among Chinese adolescents. In addition, the current study explored whether these relationships varied by gender. Using a longitudinal design, a total of 2381 secondary school students (48.8% girls, Mage = 13.38 ± 0.59) participated in the study. The results found significant positive directional effects from academic achievement to parental involvement among total sample, but not vice versa. The cross-lagged effect from academic achievement to parental involvement only existed among adolescent girls. Bootstrap analyses in the total sample revealed that parental involvement was related to academic achievement through the indirect effects of adolescents’ behavioral engagement. In terms of gender differences, behavioral engagement totally mediated the path from academic achievement to parental involvement for boys, while no significant mediation effect was found for girls. These results have provided empirical evidence of the evocative role of adolescents’ academic characteristics on parenting behaviors and the double-edged effect of parental involvement on adolescents’ academic performance, they also suggest that further research is needed to explore effective and appropriate ways for parents to get involved in adolescents’ learning in order to promote their children’s academic achievement.