The fault quantification of a tapered roller bearing (TRB) can provide a reliable guide for predictive maintenance. Currently, damage size estimation based on vibration signals has been proposed and developed. However, most approaches are focused on the theory of ball bearings. Unlike the point contact of a ball bearing, the contact between the tapered roller and the raceway is a line contact. So, the current practices based on the micro-motion theory of ball bearings are limited when estimating the TRB’s fault. To accurately estimate the TRB’s damage size, a dynamic model of non-penetrating damaged TRB was established to research the vibration response mechanism and explain the influence. The model takes the deflection factor of a tapered roller into consideration and uses the elastohydrodynamic lubrication model to simulate the influence of the lubrication factor. Then, a revised formula for estimating the TRBs’ fault size is proposed by uncovering the relationship between the impact time and the damage location. Simulation analysis and experimental analysis prove the correctness of the dynamic model and the effectiveness of the size estimation formula.