The development of radiology, rapid prototyping techniques, and the increasingly common use of 3D printing in dentistry inspires the use of these techniques to improve diagnostic and therapeutic processes. This study aimed to conduct a retrospective comparative analysis of dental panoramic radiographs, cone-beam computed tomography, and 3D printing in preoperative assessment of the procedure’s difficulty. Thirty clinical cases with a high degree of difficulty were selected, and based on evaluation with CBCT, a virtual 3D model of the region of surgical procedure was created, which was then printed using a 3D printer. The comparative analysis included the linear measurements performed in dental panoramic radiographs, cone-beam computed tomography, and 3D models in a preoperative assessment of the degree of retention and difficulty of impacted mandibular third molars in the mandible. Linear measurements performed on dental panoramic radiographs were significantly lower than in cone-beam computed tomography and 3D models. No statistically significant differences were obtained in linear measurements between 3D models and cone-beam computed tomography images except for the measurement of the lingual lamina thickness; however, due to the insignificant differences in measurements, with a mean of only 80 µm, the elective procedure of removal of the impacted third molar in the mandible may be safe.