Chronic pain is a common issue in adolescents. Prevalence of pain and associated factors present differently in sex and age subgroups; however, the interaction of sex and age combined has not been thoroughly assessed. This study aimed to identify psychosocial and health factors associated with chronic pain in younger and older adolescent girls and boys. Students from five schools in grades 5-10 self-completed a pain survey. Participants were 2,280 adolescents (52% girls) aged 10-18years (M=12.95, SD=1.84). Data were analysed using multivariate logistic regression models. Chronic pain was present in 33% of participants. The risk of chronic pain increased by 29% in girls, compared to 16% in boys, per year of age (p=.039). Overall, depression (OR=2.05, p<.001), anxiety (OR=1.51, p<.001), lower school satisfaction (OR=1.41, p=.034) and sleep issues (OR=2.34, p<.001) were associated with chronic pain. Stratified analyses identified unique significant associations between chronic pain and psychosocial factors. In boys aged 10-13years, higher socioeconomic status (OR=1.76, p=.024) and poorer school performance (OR=1.60, p=.027) were uniquely important; in girls aged 10-13years, lower school satisfaction (OR=2.92, p=.003) was associated with pain, and in older girls aged 14-18years, anxiety (OR=1.74, p=.009) was significantly associated with pain. When these differences were assessed statistically, only lower school satisfaction had significant differences between subgroups (p=.049). Many psychosocial and health factors are similarly important, with few differences, for chronic pain in girls and boys at different stages of adolescence. We report evidence that negative psychosocial and health factors are related to a higher prevalence of chronic pain in adolescents. Furthermore, the relationships between anxiety, socioeconomic status, lower school satisfaction and lower school performance with pain may vary between adolescents of differing sexes and ages. Understanding how possible risk factors for chronic pain contribute differently to the pain experience of adolescent girls and boys is an important step towards lowering the prevalence of this common health condition.