Autotransplantation of teeth (ATT) is a viable treatment option for replacing teeth lost due to various reasons. Periodontal ligament (PDL) on the donor tooth is one of the most crucial factors determining the success of ATT. To preserve the PDL during surgery and improve the success rate of ATT, digital dentistry has been applied to ATT. In this article, a digital workflow including surgical simulation, a three-dimensional (3D) replica fabrication, and a novel osteotomy guide design is introduced. Digital simulation of ATT on a patient's integrated model enables visualization of anatomical structures and the 3D position of the donor tooth prior to the actual surgery. The 3D-printed osteotomy guide allows the transfer of the direction and depth of the planned osteotomy into the intraoral environment. The 3D replica helps prepare the recipient site before the actual transplantation, which minimizes the extra-alveolar time of the donor tooth and decreases trauma during the try-in process. The proposed virtual planning and the use of the guide and the 3D replica can facilitate the surgical procedures while minimizing complications.