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Objective The objective of this study was to compare types of veneer preparations and their combination with three materials. Materials and Methods Two finite element models were specially prepared used representing window and wrap around preparation for veneers. The “central incisor” tooth geometry was acquired using a laser scanner, and then its surface was adjusted to form a solid model prior to the removal of each preparation separately. Three materials (Lava Ultimate, IPS e-max, and Celtra) were tested in combination with the preparation type. Bone geometry was simplified as two coaxial cylinders in all models. Each model was subjected to two loading conditions of occlusion (edge-to-edge bite and normal bite). Statistical Analysis and Results It was observed that cortical, cancellous bone, and periodontal ligament are insensitive to preparation or materials. Their stresses and deformation were within physiological limits. Significant changes appeared on the central incisor tooth structure, cement layer, and veneer layer stresses and deformations under loading cases. Conclusions Edge-to-edge bite stresses are severe with window-type preparation, and normal bite did not show any critical values on tooth structure, cement layer, or veneer layer. Veneer layer finish line and its contact with the cement layer and tooth structure play a role in the loading transfer mechanism. Preparation type alters the values of stresses on tooth structure, cement, and veneer layers. With window preparation, extreme stresses appear at finish line, while stresses appear under the loading site with wrap around preparation. Veneer and cement layers withstand the load energy with wrap around preparation and reduce tooth structure stresses. Thus, the lifetime of veneer and cement layers might be longer with window preparation.