Associations between adversity and youth psychopathology likely vary based on the types and timing of experiences. Major theories suggest that the impact of childhood adversity may either be cumulative in type (the more types of adversity, the worse outcomes) or in timing (the longer exposure, the worse outcomes) or, alternatively, specific concerning the type (e.g., parenting, home, neighborhood) or the timing of adversity (e.g., specific developmental periods). In a longitudinal sample from the Future of Families and Wellbeing Study (N = 4,210), we evaluated these competing hypotheses using a data-driven structured life-course modeling approach using risk factors examined at child age 1 (infancy), 3 (toddlerhood), 5 (early childhood), and 9 (middle childhood). Results showed that exposures to more types of adversity for longer durations (i.e., cumulative in both type and timing) best predicted youth psychopathology. Adversities that occurred at age 9 were better predictors of youth psychopathology as compared to those experienced earlier, except for neglect, which was predictive of internalizing symptoms when experienced at age 3. Throughout childhood (across ages 1–9), aside from the accumulation of all adversities, parental stress and low collective efficacy were the strongest predictors of internalizing symptoms, whereas psychological aggression was predictive of externalizing symptoms.