Unilateral transmigration of mandibular canines is a rare phenomenon. Occurrence of bilateral transmigration of mandibular canines is even more rare. There are diagnostic, therapeutic, and prognostic implications in the occurrence of these transmigratory patterns. Proper understanding of the mechanisms involved in the impaction and intra-osseous movement of these teeth within the bone will help clinicians to intervene and formulate better treatment options. A review of previously reported cases of bilaterally transmigrating mandibular canines from the literature was undertaken. Five new cases are reported in this article. Classification of the bilaterally transmigrating mandibular canines is proposed for better understanding, ease of communication, and appropriate management of this aberrant migratory pattern.