Background: Headache, or cephalalgia, is one of the 20 most disabling diseases in the world and affects a large portion of the world’s population. People generally use over-the-counter medications to treat headaches and other minor symptoms. A pharmacist should help patients choose the most effective, safe, and convenient pharmacotherapeutic option. Objective: To assess the counselling skills of community pharmacists for headache management by using the simulated patient approach. Methods: A cross-sectional study was conducted from March 2010 to July 2010. Data were obtained from a convenience sample consisting of one pharmacist from each of the 24 participating community pharmacies. In order to evaluate the pharmacists’ counselling skills, a simulated patient role played a standardized headache case requesting self-medication. The interactions of the simulated patient with the pharmacists were audiovisually recorded using a hidden micro camera, and these recordings were analysed using a validated questionnaire. Results: Of the 24 evaluated pharmacists, 19 (79.1%) were women. Information was spontaneously provided by 15 (62.5%) pharmacists. At least one question was asked by the pharmacist to assess the signs and symptoms. Most pharmacists (n=17, 70.8%) recommended sodium dipyrone, either alone or in combination with other drugs. The most discussed items in the simulation visits were contraindications (n=17, 70.8%), indications (n=10, 41.6%), and drug administration times (n=8, 33.3%). None of the pharmacists recommended any non-pharmacological therapeutic alternatives. The overall impressions of the pharmacists’ professional counselling skills ranged from poor to fair. Conclusion: This study showed that the pharmacists’ counselling skills and the guidance provided by the pharmacists to the simulated patient were insufficient for the satisfactory management of headache.