Catamenial pneumothorax (CP) is one of the clinical manifestations of endometriosis, therefore the systemic hormonal therapy is indispensable and should be the 1st choice for CP treatment. However, it is refractory and repeats a recurrence, so that a combined or sequential adjuvant treatment becomes necessary. From 2003 to 2009, 5 patients with CP were treated at our institution. All patients had right-sided pneumothorax and the history of pelvic endometriosis. By thoracoscopic examination, diaphragmatic abnormalities, such as defect, pinhole, or brown spot, were identified in all patients. We performed hormonal therapy combined with chemical pleurodesis using OK-432, as an initial treatment. Two patients have been free of recurrence for 24 and 53 months, respectively. Three patients who refused or interrupted hormonal therapy caused a recurrence, but were successfully managed with the addition of pleurodesis and continuing hormonal therapy. At present, all patients are asymptomatic with 13 to 92 months recurrence-free period. From the long-term results, our therapeutic strategy consisted of hormonal therapy and chemical pleurodesis is considered appropriate.