This study examined interrelations between three indicators of main challenges during adolescence: academic achievement, self-perceived peer acceptance, and self-esteem. An additional aim was to investigate whether the findings hold for girls and boys and across school types (academically oriented track vs. non-academically oriented track). We used a large German longitudinal study (N = 7,977; mean age at t[subscript 1]= 13.5 years) with three measurement points over a period of four years (start of seventh grade, end of seventh grade, end of tenth grade). Cross-lagged panel and multi-group models revealed seven main findings: (1) We found general positive associations between academic achievement, perceived peer acceptance, and self-esteem. (2) Higher academic achievement predicted higher self-esteem, but not vice versa. (3) Self-esteem and peer acceptance showed mutual associations, but only in older adolescents between the end of seventh and end of tenth grades. (4) Peer acceptance slightly predicted lower levels of academic achievement in students on the non-academically oriented track. (5) The results held for both girls and boys, but (6) changed over the course of adolescence and (7) differed between school types. Taken together, our findings offer comprehensive insight into the relations between salient developmental tasks in adolescence.