Although sex is one of the strongest correlates of crime, contentions remain regarding the necessity of sex-specific theories of crime. The current study examines delinquent trajectories across sex among Puerto Rican youth socialized in two different cultural contexts (Bronx, United States; and San Juan, Puerto Rico). Results indicate similar substantive offending trajectories across males and females within each cultural context, that males exhibit a higher frequency of offending and higher levels of risk factors for delinquency, and more similarities than differences in how risk/protective factors relate to patterns of offending across male versus female youth. Study limitations and implications for sex-specific criminological theories are also discussed.