This study used 2-D finite element modeling to simulate cuspal flexure and stresses at the surface and tooth-restoration interface of a restored maxillary molar using three restorative materials; the influence of four inlay/onlay preparation configurations on stress distribution within the complex was also investigated. A buccolingual cross-section of an intact molar was digitized and used to create 2-D models restored with different restorative materials (feldspathic porcelain, high- and low-elastic modulus composites) and tooth preparations (small and large inlays, small and large onlays). Two simulated 25-N oblique loads were applied to the cusps. The tangential stress for each finite element node located at the tooth surface, interfacial stress, and relative cuspal flexure were analyzed. All materials and tooth preparations exhibited similar surface tangential stress patterns, with a definite compressive area at the external cusp ridges, a tensile zone at the occlusal surface, and compression stress peaks at the CEJ. The low-elastic modulus composite showed reduced tensile stresses at its surface but increased tension at the dentin-adhesive interface when compared to ceramics. All types of onlays demonstrated a majority of compressive interfacial stresses, while inlays showed a majority of tensile stresses. The interfacial tension at the dentin level increased with the flexibility of the restorative material. Only the large ceramic onlay displayed almost pure compression at the interface. Composite-restored teeth exhibited increased crown flexure, while porcelain-restored teeth showed increased crown stiffness. Porcelain inlays/onlays featured more detrimental stresses at the occlusal surface but better potential protection against debonding at the dentin-restoration interface compared to composite inlays/onlays. Ceramic onlays/overlays seem to represent an effective answer to restore severely damaged posterior teeth.