Although headache frequency is increasing in preschool age children, an extensive evaluation of the clinical features in affected patients has yet to be achieved. This retrospective study examined 243 patients who were separately analysed in two distinct groups according to the age of onset and the age of first clinical evaluation. Group 1 included preschool age children, while Group 2 consisted of pubertal age patients. In all the patients the importance of a positive family history for headache as a risk factor was confirmed. In addition, when compared with Group 2, Group 1 showed greater male gender prevalence and earlier onset of the attacks. Regarding clinical features, in Group 1, compared with Group 2, the attack duration was shorter with lower symptom association such as photo- or phonophobia, nausea and no pain increase during physical activity. In the same group, tension-type headache was the predominant diagnosis, in contrast to the high migraine prevalence of Group 2. This study also showed that the International Headache Society 1988 classification criteria are not fully adequate for juvenile headaches. In fact, the headaches of more than 10% of patients in Group 1 still remained unclassifiable, while those of all the subjects in Group 2 were properly classifiable.