Objectives: Limited international studies have used family-based surveys to explore depressive symptomatology in relation to mother-adolescent dyads. Even less is known about this in Asian communities such as Taiwan, where education is highly valued. The present study uses an inter-generational framework and investigates the effect of educational aspiration mismatch on depressive symptomatology within mother-adolescent dyads. Methods: A total of 1,108 mother-adolescent dyads were surveyed when the adolescent participants were 13 years old, and then these dyads were followed up for two years. Depressive symptomatology affecting both mother and adolescent child were measured using the Symptom Checklist-90 Revised. Educational aspiration mismatch was operationalized into three groups: the mother having a higher educational aspiration than their adolescent child, both members of the dyad having the same educational aspiration, and the mother having a lower educational aspiration than their adolescent child. Results: The findings from the multivariate logistic regressions showed that, when a mother’s education aspiration was higher than that of her child, then both the mother and child were less likely to report depressive symptoms (mothers: AOR = 0.60, p<0.1; children: AOR= 0.42, p<0.05). However, children were more likely to report depressive symptomatology as their mothers’ education level increased (senior/vocational high school: AOR =1.42, p<0.1; college and above: AOR =1.81, p<0.01) as well as when the mothers’ emphasis on academic achievement increased (AOR =1.77, p<0.1). Discussion: Dyads in which the mother had a higher level of education aspiration than her child resulted in a lower level of depressive symptoms. In the future, interventions that aim to promote the mental health of adolescents and their parents should take educational aspiration within dyads into consideration.