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Abstract Background There is continuing concern about high pregnancy rates and increasing numbers of sexually transmitted infections being detected in Scottish adolescents. Consistent evidence about factors associated with risky sexual behaviours, including early first sexual intercourse, may help to identify adolescents at risk and help improve interventions. This study aimed to provide detailed analysis of the evidence of the associations between individual factors and early sexual intercourse using cross-sectional questionnaire data from 4,379 Scottish adolescents who participated in a sexual health intervention evaluation. Findings Multivariate secondary analysis showed that aspects of family and school life such as decreasing parental monitoring (OR 1.45, 95% CI 1.24–1.70) and decreasing enjoyment of school (OR 2.55, 95% CI 2.15–3.03) were associated with reporting previous sexual intercourse. Furthermore, females were more likely to report previous sexual intercourse than males (OR 1.48, 95% CI 1.14–1.91). Several factors commonly used to inform sexual health intervention design, such as socioeconomic status, self-esteem and religion, were not independently associated. Conclusion These results contribute to the evidence base for the association of several factors with early initiation of sexual activity. The findings suggest that interventions aiming to delay first intercourse may need to consider targeting aspects of individuals' connection to their school and family. Furthermore, the results do not support the need to consider socio-economic background, religion or self-esteem of the individuals in intervention design.