Thoracic endometriosis syndrome refers to the varying clinical and radiological manifestations associated with the growth of endometrial glands and stroma in the lungs or on the pleural surface. There are four clinical entities namely: catamenial pneumothorax, catamenial hemothorax, catamenial hemoptysis and lung nodules. Among the four catamenial pneumothorax is the most frequent presentation, accounting for approximately 80% cases. Catamenial pneumothorax is a recurrent pneumothorax occuring within 72 hours after the onset of menstruation but somewhat different time frames are possible. In this case report, a 41 year old nulligravid presented with recurrent difficulty of breathing, right sided chest pain and cough that coincided with her menstrual cycles. Chest x-ray and chest CT scan showed right pneumothorax. She underwent Video Assisted Thoracospic Surgery, talc and mechanical pleurodesis, chest tube thoracostomy, followed by continous combined oral contraceptive pills postoperatively. There was no recurrence of symptoms at 9 months follow-up.