Background: Positive youth development emphasizes that adaptive features of adolescence may contribute to teenage pregnancy prevention. Methods: Using data from approximately 1300 seventh-ninth graders, we describe positive youth development assets (external and internal) and their association with sexual risk taking. School-, sex-, and race/ethnicity-stratified logistic or linear models assessed associations between developmental assets and 6 outcomes (continuous attitudes about teenage sex and marriage, abstinence intentions, and nonsexual risk-taking behavior; dichotomous high risk-dating behavior, friends' sexual activity, and prior sexual activity). Results: Associations between developmental assets and youth sexual behavior differed by school, sex, and race/ethnicity. White female respondents showed the most consistent associations between higher amounts of each of the positive youth development assets and attitudes and behaviors conducive to delaying sexual activity while black youth showed the fewest associations. Conclusion: These results contribute to the positive youth development literature by identifying that relationships between assets and adolescent risk differs by race and sex.