Background: Dropout from organized youth sport has significant adverse health implications. Enjoyment and behavioral intentions have consistently been linked with participation and dropout; however, few studies have investigated these links using a prospective design. This study explored whether enjoyment and intentions to continue predicted dropout behavior at 1-year follow-up. Methods: Questionnaires were completed by 327 regular sport participants (mean age = 13.01 y at baseline). After 1 year, 247 individuals (75.5%) continued participating in their main sport and 26 individuals (8%) dropped out. A hierarchical logistic regression model estimated the probability of dropout. In step 1, the following covariates were included: age, sex, competition level, perceived competence, parental support, coach–athlete relationship, friendship quality, and peer acceptance. In step 2, enjoyment and intentions to continue were included. Results: Step 1 indicated that age, parental support, coach–athlete relationship quality, and peer acceptance were significantly associated with dropout. Step 2 explained further variance in dropout, with both enjoyment and intentions inversely associated with dropout. Peer acceptance was the only covariate to remain significantly associated with dropout in step 2. Conclusions: Findings support the use of enjoyment and behavioral intentions as indicators of sport participation/dropout behavior and may aid the development of interventions aimed at preventing future dropout.