Transmigration of mandibular canines across the midline is rare. Two 14-year-old female patients from South India were found to exhibit this phenomenon. In one patient, the mandibular right canine had crossed the midline and migrated to the left, up to the mesial root apex of the permanent first molar, near the lower border of the mandible. In the other patient, the permanent mandibular left canine had crossed the midline and migrated up to the root of the mandibular right canine. Both of these patients are being observed regularly for further migration. The literature on this rare condition is reviewed and its etiologic possibilities and treatment modalities are discussed.