Background Catamenial pneumothorax (CP) is defined as a recurrent, spontaneous pneumothorax occurring within a day before or 72 h after the onset of menstruation. Most first episodes go undiagnosed and treated as primary spontaneous pneumothorax, and only after recurrence is the clinical suspicion of CP raised. No gold-standard management approach exists, especially in terms of managing diaphragmatic involvement. Methods This study is a single-centre cohort retrospective study of 24 female patients who underwent surgery for pneumothorax due to diaphragmatic endometriosis between January 2008 and December 2016. Two groups were compared: a group that underwent pleurodesis alone (8 patients) and a group that underwent diaphragmatic surgery and pleurodesis (16 patients). Results There were differences in BMI and smoking habits between the two groups. The right diaphragm was involved more often (6vs15, p  = 0.190). VATS was the preferred surgical approach and only one conversion occurred in the diaphragmatic surgery group ( p  = 0.470). Diaphragmatic abnormalities were present in all the patients, brown/violet spots (100%) in the pleurodesis group and perforations (100%) in the diaphragmatic surgery group ( p  < 0.001). There were no differences in days of chest tube removal and length of stay. The recurrence rate was 100% in the pleurodesis alone group while it was only 12.5% in the diaphragmatic surgery group (< 0.001). Conclusions In our experience, diaphragmatic surgery and pleurodesis followed by hormonal therapy was an effective approach in preventing recurrence in patients with catamenial pneumothorax and diaphragmatic involvement.