Catamenial pneumothorax and hemothorax, the manifestations of thoracic endometriosis, are being reported with increasing frequency, probably because of increased awareness. Although many theories about the pathogenesis were suggested, the etiology of this syndrome remains obscure. Prevention of recurrence is difficult, as the recurrence rate is high, treatment duration is potentially long, and residual thoracic pain during menstruation is sometimes seen. Two cases of recurrent catamenial pneumothorax and hemopneumothorax with concurrent pelvic endometriosis are reported. A right thoracoscopy and a tube thoracostomy were performed in one of the patients. The other patient underwent a tube thoracostomy. The surgical procedures were combined with the suppression of the ovulation by hormonal therapy. No recurrences were seen in the follow-up. Catamenial pneumothorax and hemothorax must be considered in all premenopausal women with recurrent pneumothorax or hemopneumothorax. The combination of medication (Gn-RH analogues, danazol, nonsteroidal antiinflammatory prostaglandin synthetase inhibitors) and thoracoscopic intervention seems to be the most effective treatment.