Educational level is strongly associated with age of first intercourse and risk of unintended pregnancies. This study examined these associations in a large representative sample of Dutch adolescents and also included associations of educational level with other sexual health aspects. Adolescents aged 12 to 25 (3,926 boys and 3,915 girls) completed an online questionnaire that included measures of romantic and sexual experience; the evaluation of their sexual debut; the risk of sexually transmitted infections (STIs) and pregnancy; and sexual attitudes, satisfaction, self-efficacy, knowledge, victimization, and functioning. The results showed that adolescents on a vocational track or who completed fewer years of education were more at risk of several adverse sexual health outcomes than adolescents on an academic track. They had their first sexual experiences at an earlier age; evaluated these experiences less favorably; had less sexual health knowledge and fewer refusal skills; and had a higher risk of unintended pregnancy, STIs, and victimization. Possible explanations for these consistent differences are discussed. Sex education and services should pay specific and targeted attention to less educated young people and tailor their efforts specifically to the needs, characteristics, and realities of this group.