This study's aim was to search for the appropriate functional form of the effect of proximal cumulative contextual risk (PCCR), measured with number of adverse life events experienced in the last 6 months, on adolescent psychopathology and prosocial behavior, measured with the Strengths and Difficulties Questionnaire. The study sample was 171 year ten (aged 14-15) adolescents from predominantly socio-economically disadvantaged families in the UK. Adjustment was made for parental education, and for child's age, gender, and academic achievement, which was measured with results in Standard Attainment Tests in English, mathematics and science taken in the previous year. PCCR predicted total difficulties, emotional symptoms, conduct problems and hyperactivity. The relationship between PCCR and total difficulties and emotional symptoms was non-quadratic; the PCCR/externalizing problems relationship was quadratic. The findings highlight the importance of considering both outcome specificity and non-linear patterns of associations when modelling cumulative contextual risk effects on adolescent psychopathology.