Background Although radiographs and computed tomography (CT) images are reviewed before temporary anchorage device (TAD) implantation, implantation of TADs exactly as planned is difficult. This study aimed to evaluate the accuracy of TAD implantation using an original surgical guide fabricated using cone-beam CT data and computer-aided design software. Methodology The study participants included six experienced orthodontists who had implanted ≥20 TADs, and six inexperienced orthodontists who had never implanted a TAD. Maxillary dental typodont models with radiopaque tooth crowns and roots were used. A total of four TADs were implanted on the buccal sides between the second bicuspid and first molars and between the first and second molars bilaterally. The accuracy of TAD implantation was examined in two groups in 12 dental typodont models, TAD implantation was performed using a surgical guide (guide group), and in 12 dental typodont models, TAD implantation was performed without a surgical guide (freehand group). All dental typodont models implanted a total of 96 TADs. The TAD position was evaluated using the CT coordinate system and 3D image measurement software. Using the long axis of the TAD as a reference, the distance between the coronal and apical ends of the implanted TAD and those of the planned TAD, i.e., the ideal implantation position, was measured in both groups along the x, y, and z axes. The medians of the values were compared between the groups. Additionally, the presence of root contact was compared between the experienced and inexperienced orthodontists. Results On the x-axis, the linear deviations (median) of the coronal and apical ends of the TAD in the freehand group were 1.06 mm and 1.36 mm, respectively. In contrast, in the guide group, the deviations were 0.65 mm and 0.90 mm, respectively, and the difference was statistically significant (p = 0.002 and p = 0.005, respectively). On the y-axis, the deviations in the freehand group were 1.13 mm and 1.08 mm, respectively. In contrast, the deviations in the guide group were 0.71 mm and 0.79 mm, respectively, and only the coronal deviations were significantly different between the groups (p = 0.006). On the z-axis, the deviations in the freehand group were 1.44 mm and 1.86 mm, respectively. In contrast, the deviations in the guide group were 0.75 mm and 1.16 mm, respectively, and the difference was statistically significant (p = 0.006 and p = 0.002, respectively). Conclusions The use of a surgical guide allowed for more accurate TAD implantation. Additionally, TAD implantation using a guide prevented root damage.