Increasingly, health care providers are using approaches targeting parents in an effort to improve adolescent sexual and reproductive health. Research is needed to elucidate areas in which providers can target adolescents and parents effectively. Parental monitoring offers one such opportunity, given consistent protective associations with adolescent sexual risk behavior. However, less is known about which components of monitoring are most effective and most suitable for provider-initiated family-based interventions. We performed a meta-analysis to assess the magnitude of association between parental monitoring and adolescent sexual intercourse, condom use, and contraceptive use. We conducted searches of Medline, the Cumulative Index to Nursing and Allied Health Literature, PsycInfo, Cochrane, the Education Resources Information Center, Social Services Abstracts, Sociological Abstracts, Proquest, and Google Scholar. We selected studies published from 1984 to 2014 that were written in English, included adolescents, and examined relationships between parental monitoring and sexual behavior. We extracted effect size data to calculate pooled odds ratios (ORs) by using a mixed-effects model. Higher overall monitoring (pooled OR, 0.74; 95% confidence interval [CI], 0.69-0.80), monitoring knowledge (pooled OR, 0.81; 95% CI, 0.73-0.90), and rule enforcement (pooled OR, 0.67; 95% CI, 0.59-0.75) were associated with delayed sexual intercourse. Higher overall monitoring (pooled OR, 1.12; 95% CI, 1.01-1.24) and monitoring knowledge (pooled OR, 1.14; 95% CI, 1.01-1.31) were associated with greater condom use. Finally, higher overall monitoring was associated with increased contraceptive use (pooled OR, 1.42; 95% CI, 1.09-1.86), as was monitoring knowledge (pooled OR, 2.27; 95% CI, 1.42-3.63). Effect sizes were not uniform across studies, and most studies were cross-sectional. Provider-initiated family-based interventions focused on parental monitoring represent a novel mechanism for enhancing adolescent sexual and reproductive health.