Machining chatter is one of the main factors that restricts the machining quality and efficiency of thin-walled cylinder workpiece. The semi-discrete method was used to predict the stability of the dynamic system with time delay, combined with the cutting experiments on thin-walled workpieces, the influence of the change of dynamic parameter matching relationship between the tool and the workpiece on the machining stability was studied. The simulation results show that the stability of the cutting system increases with the increase of the tool stiffness or natural frequency, but the cutting stability can not be effectively improved by increasing the tool stiffness excessively; when the natural frequency of the tool and the workpiece is close to each other, the stability of cutting system is decreased; the stability of flexible workpiece can be improved by adjusting the tool dynamic characteristic parameters properly; in the process of cutting, the time-varying cutting position and workpiece dimension can cause the change of dynamic characteristics of the cutting system. Based on the time-varying stability prediction diagram, the reason for different machining chatter patterns on the surface of thin-walled cylinder in the cutting experiments was explained.