Oleo-pneumatic landing gear is a complex mechanical system conceived to efficiently absorb and dissipate an aircraft’s kinetic energy at touchdown, thus reducing the impact load and acceleration transmitted to the airframe. Due to its significant influence on ground loads, this system is generally designed in parallel with the main structural components of the aircraft, such as the fuselage and wings. Robust numerical models for simulating landing gear impact dynamics are essential from the preliminary design stage in order to properly assess aircraft configuration and structural arrangements. Finite element (FE) analysis is a viable solution for supporting the design. However, regarding the oleo-pneumatic struts, FE-based simulation may become unpractical, since detailed models are required to obtain reliable results. Moreover, FE models could not be very versatile for accommodating the many design updates that usually occur at the beginning of the landing gear project or during the layout optimization process. In this work, a numerical method for simulating oleo-pneumatic landing gear drop dynamics is presented. To effectively support both the preliminary and advanced design of landing gear units, the proposed simulation approach rationally balances the level of sophistication of the adopted model with the need for accurate results. Although based on a formulation assuming only four state variables for the description of landing gear dynamics, the approach successfully accounts for all the relevant forces that arise during the drop and their influence on landing gear motion. A set of intercommunicating routines was implemented in MATLAB® environment to integrate the dynamic impact equations, starting from user-defined initial conditions and general parameters related to the geometric and structural configuration of the landing gear. The tool was then used to simulate a drop test of a reference landing gear, and the obtained results were successfully validated against available experimental data.