Background: The aim of this study was to investigate cuspal deflection caused by material shrinkage and temperature rise occurring in the pulp chamber during photopolymerization. The aim of this study was also to investigate the effect of flowable and packable bulk-fill composites on cuspal deflection occurring in mesio-occlusal–distal (MOD) cavities restored through the bulk-fill or through the incremental layering technique. Additionally, mechanical and thermal properties of bulk-fill composites were considered. Methods: Two bulk-fill composites (high-viscosity and low-viscosity), largely differing in material composition, were used. These composites were characterized through linear shrinkage and compressive test. Cuspal deformation during restoration of mesio-occlusal–distal cavities of human premolars was evaluated using both the bulk-fill and the incremental layering techniques. Temperature rise was measured through thermocouples placed 1 mm below the cavity floor. Results: Shrinkage of the flowable composite was significantly higher (p < 0.05) than that of packable composite, while mechanical properties were significantly lower (p < 0.05). For cusp distance variation, no significant difference was observed in cavities restored through both restorative techniques, while temperature rise values spanned from 8.2 °C to 11.9 °C. Conclusions: No significant difference in cusp deflection between the two composites was observed according to both the restorative techniques. This result can be ascribed to the Young’s modulus suggesting that the packable composite is stiffer, while the flowable composite is more compliant, thus balancing the cusp distance variation. The light curing modality of 1000 mW/cm2 for 20 s can be considered thermally safe for the pulp chamber.