This study investigates the dynamic and hydrodynamic behavior of a light land-based aircraft landing gear, focusing on the pneumatic–hydraulic shock absorber used in the Cessna 172. The objective is to examine the shock absorber’s performance under varying operational conditions. A review of the relevant literature highlights that despite decades of extensive research, the topic remains highly relevant due to continuous advancements in modeling techniques and design optimization. A system of mathematical models is developed, incorporating the compressibility of gas and oil, sealing friction, variable discharge coefficients, the effects of metering pin and orifice geometries and ground-contact loads. An initial experiment characterizes the baseline response of the shock absorber and validates the model through comparison with physical measurements. Building on the data gathered during this preliminary phase, the subsequent studies investigate how landing velocity and internal geometry influence inter-chamber pressure distribution and hydrodynamic damping. The results show that the geometric characteristics of the inter-chamber orifices and metering pin are the dominant factors influencing damping performance. However, at low strut piston velocities, the behavior of the shock absorber is primarily governed by frictional forces within the sealing elements. The findings highlight the importance of accurately characterizing the geometric and tribological properties of internal components, as well as the dissolved gas content in the hydraulic fluid, to improve the accuracy and reliability of future shock absorber models.