Objective: This study aimed to evaluate the shear bond strength (SBS) of orthodontic brackets bonded to three-dimensionally (3D)-printed materials after various surface treatments and artificial aging compared with that bonded to computer-aided design/ computer-aided manufacturing (CAD-CAM) polymethyl methacrylate (PMMA)-milled materials. Methods: Eighty cylindrical specimens were 3D printed and divided into the following four subgroups (n = 20 each) according to the surface treatment and artificial aging procedure. Group A, sandblasted with 50 µm aluminum oxide particles (SA) and aging; group B, sandblasted with 30 µm silica-coated alumina particles (CO) and aging; group C, SA without aging; and group D, CO without aging. For the control group, 20 CAD-CAM PMMA-milled cylindrical specimens were sandblasted with SA and aged. The SBS was measured using a universal testing machine (0.25 mm/ min), examined at ×2.5 magnification for failure mode classification, and statistically analyzed (p = 0.05). Results: The retention obtained with the 3D-printed materials (groups A-D) was higher than that obtained with the PMMA-milled materials (control group). However, no significant difference was found between the study and control groups, except for group C (SA without aging), which showed significantly higher retention than the control group (PMMA-SA and thermocycling) (p = 0.037). Study groups A-D predominantly exhibited a cohesive specimen mode, indicating specimen fracture. Conclusions: Orthodontic brackets bonded to 3D-printed materials exhibit acceptable bonding strengths. However, 3D-printed materials are prone to cohesive failure, which may result in crown fractures.