Subcutaneous facial emphysema is a well-known consequence of oral and maxillofacial traumatic injury. In some rare cases, the subcutaneous air collection could spread through the retropharyngeal and paralatero-cervical spaces, reaching the mediastinum. This clinical entity is known as pneumomediastinum and represents a severe and, sometimes, life-threatening condition. Other reported causes of pneumomediastinum are esophageal and tracheal traumatic or iatrogenic rupture. Finally, the so-called spontaneous pneumomediastinum is caused by a sudden increase in alveolar pressure and is usually seen in young men. We present two cases of pneumomediastinum as a consequence of unusual traumatic damage of orofacial tissues, followed by repeated sneezing and Valsalva maneuver.