This work aimed at studying the effect of a silica specific surface area (SSA), as determined by the nitrogen adsorption method, on the viscoelastic and fatigue behaviors of silica-filled styrene–butadiene rubber (SBR) composites. In particular, silica fillers with an SSA of 125 m²/g, 165 m²/g, and 200 m²/g were selected. Micro-computed X-ray tomography (µCT) was utilized to analyze the 3D morphology of the fillers within an SBR matrix prior to mechanical testing. It was found with this technique that the volume density of the agglomerates drastically decreased with decreasing silica SSA, indicating an increase in the silica dispersion state. The viscoelastic behavior was evaluated by dynamic mechanical analysis (DMA) and hysteresis loss experiments. The fatigue behavior was studied by cyclic tensile loading until rupture enabled the generation of Wöhler curves. Digital image correlation (DIC) was used to evaluate the volume strain upon deformation, whereas µCT was used to evaluate the volume fraction of the fatigue-induced cracks. Last, scanning electron microscopy (SEM) was used to characterize, in detail, crack mechanisms. The main results indicate that fatigue life increased with decreasing silica SSA, which was also accompanied by a decrease in hysteresis loss and storage modulus. SEM investigations showed that filler–matrix debonding and filler fracture were the mechanisms at the origin of crack initiation. Both the volume fraction of the cracks obtained by µCT and the volume strain acquired from the DIC increased with increasing SSA of silica. The results are discussed based on the prominent role of the filler network on the viscoelastic and fatigue damage behaviors of SBR composites.