Cushioning is an important aspect in hydraulic cylinder performance. The piston has to be decelerated before it strikes the end cap in order to avoid stresses in the cylinder components and reduce vibration that can be transmitted to the machine. One of the least-studied methods is internal cushioning by grooves in the piston. In this method, the flow is throttled with adequately designed grooves when the piston reaches the outlet port position. The purpose of the present work is to present a method to estimate the pressure-drop coefficients for a certain design of piston grooves in order to provide a model to develop a dynamic system simulation of the cushion system. The method is based on a computational fluid dynamic simulation of flow through piston grooves to the outlet port for each piston’s static position. The results are compared with experimental measurements, and a correction, based on Reynolds number, is proposed. Good agreement, below 16%, was obtained for all the positions but particularly for the last grooves, for which the numerical result’s deviation to the experimental measurements was less than 10%. In general, the numerical simulation tended to underestimate the pressure drop for the first grooves and overestimate the calculation for the last grooves.