The study aims to reveal links on how academic achievements are dependent on children’s values and their relationship with parents in Lithuania from a study of 18–52-year-old Lithuanians. Three age cohort groups were distinguished, and each cohort represents different historical and socialization (pre)conditions and experiences of the education system and society context. A general assumption was tested that each generation had different (material vs. post-material) value orientations and relationship(s) with parent(s) (reactive vs. stimulating parent-child relation), which influences academic achievements. The results showcase that there is a significant relationship between academic achievements and personal values and experiences of parenting style. Stimulating parenting style is associated with a higher degree of academic success, while reactive parenting has decreased achievements in all the cohorts. Post-material value orientations (especially self-direction as the value) are strongly linked with academic success. Inter-cohort differences indicate the importance that personal values and parenting has had greater effect on the younger generation’s academic achievements compared to the older ones. A general inter-cohort tendency was found to be that parenting has had a greater effect across all the generations on being more successful in school than personal values. Stimulating parenting style via self-direction as the value has had a mediating effect on academic achievements as well.