Autotransplantation of premolars is a well-established method to rehabilitate aplasia of premolars. Nevertheless, with the introduction of titanium implants, not all surgical units offer this procedure. The aim of this study was to examine the predictability of autotransplantation of premolars on orthodontic indication as suggested by Andreasen et al., when performed by surgeons with or without prior experience of this procedure. A prospective protocol was implemented in 2001. All patients treated with autotransplantation of premolars during the years 2001–2015 were recalled to evaluate the long-term status of the teeth. The state of root development, need for endodontic treatment, presence of an apical pathology or ankylosis, and tooth loss were recorded. The results were divided into two groups according to the surgeon’s experience: senior surgeons with prior training and experience in the procedure and junior surgeons without prior experience. A total of 89 teeth (66 patients) were treated. The mean observation time was 10.1 years (range 1.0–15.1 years). The long-term survival rate was 95%. No statistically significant difference between the results of the two groups of surgeons was found. Autotransplantation of premolars on orthodontic indication could be adopted successfully in the hospital setting regardless of surgeon experience.