Parenting stress of mothers has frequently been linked to negative child outcomes. According to Abidin’s stress model, this relationship may be explained by dysfunctional parenting behaviors. In this study, we scrutinized the effects of both mothers and fathers in the pathway from parenting stress through parenting behaviors to subsequent adolescent behavior problems. We expected the association between parenting stress and adolescent behavior problems to be partially mediated by maternal and paternal parenting behaviors. Further, we expected crossover effects, i.e., that parenting stress of one parent was related to the parenting behavior of the other parent. We applied a 3-wave longitudinal design using data from 441 adolescents (52% girls) and their parents (419 fathers; 436 mothers). Parents reported on parenting stress (adolescent age range = 10.9–16.3 years). Adolescents reported on perceived parental overreactivity and warmth (age range = 12.9–18.3) and their own internalizing and externalizing problems (age range = 15.9–21.3). Despite cross-sectional significant associations between parenting stress, parenting behavior, and adolescent behavior problems, we found no evidence of longitudinal linkages. One exception was maternal parenting stress, which positively predicted later adolescent externalizing problems. Consequently, the mediating role of parenting behaviors was not supported. We found no crossover effects in the pathway from parenting stress to parenting behaviors. The discrepancies between our longitudinal and cross-sectional findings raise questions about the actual impact that parents have on their children’s outcome. Though, targeting mothers’ parenting stress may help to reduce adolescent externalizing problems and its ramifications at least to some extent.