Simultaneous bilateral spontaneous pneumothoraces (SBSP) are uncommon. This report presents the case of a previously well 19-year-old man with a diagnosis of SBSP and symptoms suggestive of occupational asthma. Despite bilateral bullectomy and pleurodesis using a video-assisted thoracoscopic surgical technique, the pneumothorax reoccurred unilaterally and open surgery was performed. This case illustrates a rare condition of bilateral pneumothoraces presenting as a first presentation of occupational asthma and the issues surrounding its management.