Patients with chronic migraine (CM) and medication overuse (MO) have a high frequency of psychiatric comorbidity or psychopathological traits, the presence of which may have important implications for the course of the CM and the MO, both for response to treatment and possible relapses. Overuse of symptomatic drugs is regarded as one of the most important risk factor for the transformation of episodic migraine into CM and drug-seeking tendency due to fear of headache in chronic migraine patients shares with obsessive-compulsive disorder (OCD) the compulsive quality of the behavior. Aim of this study was to review the clinical history of a sample of CM patients with MO in which an obsessive-compulsive trait was identified, performing a comparison with a sample of patients without obsessive-compulsive trait. We selected 14 patients with positivity to Spectrum Project OBS (obsessive-compulsive disorder) questionnaire and other 14 patients with negativity to the same tool from among a sample of patients who were enrolled in a previous study on the psychopathological profile of patients suffering from CM with MO. According to data obtained from the clinical records referring to the previous 5 years, patients with OBS questionnaire positivity showed a worse clinical course and a tendency to early relapse in MO after symptomatic medication withdrawal. Our results show that the comorbidity of OCD should be always evaluated in patients with CM and MO as it may play a relevant role--particularly if not treated--among the risk factors favoring the progression of episodic migraine to the chronic form, and/or the tendency to a pathological behavior that prompts the overuse of symptomatic medications.