Transmigration of an impacted tooth through the symphyseal suture is a rare and special developmental anomaly of unknown etiology that is unique to the mandibular canine. Maxillary canine transmigration is even rarer. Transmigrated canines are particularly significant due to the aesthetic and functional importance. A maxillary lateral incisor crossing the mid-palatal suture has never been reported in the literature. The aim of this report is to present the first case of simultaneous transmigration of a lateral incisor and canine in the maxilla. The paper also reports four unusual cases of unilateral canine transmigration in the maxilla and mandible and successful eruption of one of the transmigrated mandibular canines following orthodontic traction. Etiology of transmigration and its clinical considerations are also discussed.