This paper presents a comprehensive experimental and simulation study on the stick–slip characteristics of pneumatic cylinders operating at low velocities. A pneumatic servo experimental system is constructed to systematically investigate stick–slip motion by measuring piston position, piston velocity, pressures in the two-cylinder chambers, and friction force. Extensive experiments are conducted on three pneumatic cylinders of different types and sizes to examine the influences of airflow rate, air source pressure, external load, and initial piston position on stick–slip behavior. Based on experimental observations, a complete mathematical model of the pneumatic servo system is developed. Unlike conventional approaches that simulate stick–slip motion using friction models driven solely by piston velocity, the proposed system-level model explicitly describes the entire dynamic process from valve control inputs to airflow, pressure evolution in the cylinder chambers, piston motion, and friction force. In addition, a new dynamic friction model is proposed by improving the revised LuGre friction model through the incorporation of a dwell-time-dependent static friction force, which is experimentally observed to play a critical role in governing stick–slip motion. Simulation studies are performed using both the proposed friction model and the revised LuGre friction model. The simulated results are systematically compared with experimental data for all tested cylinders. The results demonstrate that the proposed system model with the new friction formulation significantly improves the prediction of stick–slip characteristics, including the number of stick–slip cycles and the evolution of pressure and friction force, compared with conventional friction-model-based simulations.