Adolescent sexual offending represents an ongoing social, judicial, clinical, and policy issue for services. The current study investigated the characteristics, criminal versatility, and rates of recidivism of a cohort of 156 male adolescent sexual offenders who were referred for psychological assessments by the courts between 1996 and 2007 in Singapore. Analyses revealed that specialists (sex-only offenders; n = 71, Mfollow-up = 56.99 months, SDfollow-up = 31.33) and generalists (criminally versatile offenders; n = 77, Mfollow-up = 67.83 months, SDfollow-up = 36.55) differed with respect to offense characteristics (e. g., sexually assaulting familial victims) and recidivistic outcomes. Although both groups sexually reoffended at roughly the same rate (14.3% vs. 9.9%), consistent with their typology, significantly more of the generalists reoffended violently (18.2% vs. 1.4%), sexually and/or violently (27.3% vs. 11.3%), nonviolently (37.7% vs. 16.9%), and engaged in any further criminal behaviors (45.5% vs. 23.9%) during follow-up. Adjusting for total number of offenses and age at first sexual offense, Cox regression analyses showed that generalists were significantly more likely than specialists to reoffend violently (hazard ratio = 9.31; 95% confidence interval = 1.15-76.39). The differences between generalists and specialists suggest a valid typological distinction with a higher risk trajectory for the generalists. These findings therefore have important clinical implications for assessment, management, and intervention planning for adolescent sexual offenders.