This study aimed to assess how different resin matrix formulations affect the fatigue resistance of resin dental composites. Model dental composites were formulated using six distinct monomer mixtures: two Bis-GMA (bisphenol A-glycidyl methacrylate):TEGDMA (triethylene glycol dimethacrylate) (60:40 and 80:20 mole%), two UDMA (urethane dimethacrylate):TEGDMA (60:40 and 80:20 mole%), one Bis-GMA:UDMA:TEGDMA (35:35:30 mole%), and one Fit852:UDMA:TEGDMA (35:35:30 mole%). Cyclic fatigue resistance (CFR) of the resin composites was measured in a biaxial test mode using staircase analysis. Additional evaluations included biaxial flexural strength (BFS), degree of conversion (DC), water sorption (WS), and viscoelastic properties of the unfilled resins, such as the storage modulus (E′), loss modulus (E″), tan δ (E″/E′), and stiffness (k′). Data were subjected to one-way ANOVA with Tukey post hoc analyses. Pearson correlation and stepwise regression analyses were conducted to examine the relationships among variables. The UT6040 model composite exhibited the highest CFR (82.61 ± 8.83 MPa), significantly outperforming other formulations. Tan δ of the resin matrix showed the strongest correlation with CFR (r = 0.974), and was also shown to be the most influential predictor for the CFR of the particulate composites. The composition of the resin matrix has a significant impact on the CFR of dental composites. Among the properties evaluated, the viscoelastic parameter tan δ emerged as a strong and reliable predictor of CFR, emphasizing the importance of targeting viscoelastic behavior in the design of dental composite formulations.