Youth gangs are ubiquitous around the world and have been problematic for the social and criminal justice agencies. Despite widespread public concern, there has been relatively scarce empirical scrutiny of youth gangs internationally and little outside of America and Europe. In particular, the activities of youth gangs, the function of gang membership, the criminogenic needs of gang-affiliated youth, and the risk of criminal recidivism for gang-affiliated youth remain unclear. Against this background, this study explored the sociodemographic characteristics, risk and rate of criminal recidivism in a cohort of 165 male youth offenders in Singapore, of which 58 were gang-affiliated. Multivariate analyses revealed that gang-affiliated youth offenders were significantly more likely to have histories of substance use, weapon use and violence than nongang-affiliated youth offenders. Gang-affiliated offenders also scored higher on measures of risk for recidivism (SAVRY and YLS/CMI), and engaged in violent and other criminal behaviors more frequently during follow-up. These differences indicate a significant relationship between gang affiliation and criminal recidivism in youth offenders. Furthermore, these findings have important clinical and policy implications, indicating an increased requirement for additional and more intensive assessment and tailored interventions for gang-affiliated youth offenders.