Abstract Background Increasing evidence suggests a complex role of family influences, such as the exposure to parent psychopathology through parenting behavior, in parent-to-child psychopathology transmission. Parenting behaviour could represent a relevant target of psychoeducative intervention. Given these premises, we aimed to evaluate homotypic and heterotypic relationships between parent and child psychopathology, mediated by parenting behaviours, taking into account the constructs of parent and offspring internalizing and externalizing psychopathology. Methods Internalizing and externalizing symptoms in 272 clinically-referred subjects (mean age = 14.5 ± 2.3; F = 23.5%) and their parents (mothers n = 272, fathers n = 242) were assessed through the Child Behavior Checklist and the Adult Self Report; four areas of parenting behaviours were investigated through the Family Life Questionnaire. Multiple mediation models were built, considering mother and father psychopathology scales as independent variables, parenting measures and family functioning as mediators (Affirmation, Rules, Discipline and Special Allowances), child psychopathology scales as dependent variables and demographic variables as covariates. Results Regression models showed a significant effect of maternal internalizing symptomatology on child externalizing behavioral problems; high levels of maternal pathology predicted high levels of children’s psychopathology. A total mediating effect of parenting measures was found: high levels of internalizing symptoms in mothers predicted low levels of affirmation, which in turn predicted high levels of externalizing psychopathology in children. Conclusions Our study results confirmed the existence of interdependent links between mothers’ psychiatric symptomatology, parenting behaviour and offspring outcomes, specifically in an Italian context. On a clinical and rehabilitation basis, this work offers suggestions about parenting practices, specifically maternal, involved in the maintenance of child psychopathology.