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Objective To assess for differences in headache characteristics and psychosocial factors based on headache diagnosis, and to evaluate whether headache diagnosis moderates relations between psychosocial factors and school difficulties. Methods Retrospective chart review was conducted with 262 adolescents with chronic tension-type headache (TTH; N = 153) and migraine evaluated at a pediatric headache clinic. Adolescents completed measures of anxiety, depression, and pain coping. Parents completed a measure of parental protective behavior and school functioning. Results Adolescents with TTH reported greater depression symptoms, and their parents endorsed greater school difficulties, whereas parents of adolescents with migraine reported more protective parenting. Protective parenting was positively associated with school difficulties in both groups, but the relation was significantly stronger in adolescents with TTH. Headache duration and depression symptoms were significant predictors of school functioning in both groups. Conclusions Headache duration and depression may impact school functioning independent of headache diagnosis. Protective parenting, in particular, seems to be linked to school-related disability in adolescents with TTH, and this link may be important to consider in assessment and treatment.