Sport specialization has been linked to multiple negative health related outcomes including increased injury risk and sport attrition, yet a gap remains in our understanding of potential psychological outcomes of early specialization (≤ age 12). The current study evaluated the associations between retrospective athlete reports of sport specialization and both retroactive and current psychological health outcomes. Early specializers reported significantly higher levels of multiple maladaptive psychological outcomes (e.g., global athlete burnout, emotional and physical exhaustion, sport devaluation, amotivation). Overall, findings suggest that specialization environment factors, in addition to the age of specialization, are potentially critical factors in determining health and well-being outcomes. Findings support prominent position statements suggesting early specialization may be associated with increased health risks. Study findings may also inform the development of guidelines and recommendations to aid parents, coaches, and athletes in positively impacting athlete psychosocial outcomes.