Background: Tooth autotransplantation is a reliable procedure with high long-term success and survival rates, showing many advantages over dental implants, particularly for young patients in craniofacial development. Nonetheless, insufficient bone availability at the recipient site is a key limitation. This study aims to establish the feasibility of tooth autotransplantation combined with staged or simultaneous bone regeneration to address complex cases. Material & Methods: Two young patients with missing teeth due to hypodontia or trauma, deemed unsuitable for dental implants, were treated. Both complex cases were addressed through autologous tooth autotransplantation, either in conjunction with simultaneous guided bone regeneration or into a previously regenerated crest. Results: Five-year follow-up for the autotransplanted cuspid and more than 20-year follow-up for the premolar revealed satisfactory results for both autotransplanted teeth. These teeth played pivotal roles in restoring both function and aesthetics in young patients. Additionally, tooth vitality was preserved throughout the follow-up period, with no complications noted. Conclusion: Tooth autotransplantation in combination with previous or simultaneous guided bone regeneration proved to be effective in restoring function and aesthetics in complex situations in young patients.