The aim of this article is to assess the concordance between parent and adolescent headache ratings in a representative sample of 6483 US adolescents (aged 13–18 years). Headaches were assessed using modified criteria from the International Headache Society's International Classification of Headache Disorders, Second Edition. Caregiver report was based on a self-administered questionnaire. Overall concordance between caregivers and adolescents on the presence or absence of headaches was quite low (κ = 0.39). Female caregivers were twice as likely as male caregivers to report headaches in their offspring. Positive endorsement of headaches in offspring by caregivers was associated with adolescent-reported chronic headaches, longer headache duration, and photophobia or phonophobia. These findings suggest that relying solely on parent report may result in an underestimate of the true prevalence of headaches in the general population. In addition, collecting information from both parents and adolescents could be critical to effective treatment and prevention of the severe consequences of migraine.