Although research has documented the adverse consequences of parental academic conditional regard in different developmental periods, few studies have examined antecedents and, in particular, the possibility of intergenerational continuity of this parenting dimension. The current study aimed to identify patterns of intergenerational similarity in two types of conditional regard (i.e., positive and negative). Additionally, it examined mothers’ and adolescents’ contingent self‐esteem (CSE) and depressive symptoms as outcomes of this process. In total, 211 mothers and their 10‐ to 16‐year‐old adolescents filled out questionnaires assessing perceived conditional regard in the relationship with their own mother (i.e., grandmothers’, and mothers’ conditional positive (PACPR) and negative regard (PACNR)), contingent self‐esteem (i.e., maternal child‐invested CSE and adolescents’ academic CSE), and maternal and adolescents’ depressive symptoms. Results revealed direct intergenerational similarity for PACPR, but not for PACNR. Within generations, PACPR was related positively to CSE, which, in turn, was related positively to depressive symptoms. Moreover, PACNR was related positively to depressive symptoms. Our findings provide preliminary evidence for the intergenerational continuity of conditional regard, which has important consequences because of its relation to CSE and subsequent depressive symptoms within both generations.