When shifting gears around a tractor’s power shift transmission, it is necessary to coordinate the control of multiple clutches and formulate a reasonable clutch engagement law to ensure the reliability and power of the power system. This paper explores the impact of different clutch engagement patterns on shifting characteristics in a power-shift tractor with multiple clutches. Shifting performance is comprehensively evaluated using indicators such as shifting time, impact degree, slip energies, and transmission output torque. The aim is to enhance the quality of power shifting, operational efficiency, and the service life of the transmission system. This paper takes the YTO TX4A transmission system as the research object, analyzes its working principle, and establishes a mathematical model of a power shift transmission system under different clutch engagement rules. This model of power shift transmission is established based on Matlab2021/Simulink and the AMESim2021 software platform. A simulation analysis is carried out for four clutches working simultaneously in a tractor’s advance gear II and lift gear III. The simulation results indicate that switching rule C is superior to switching rule A and switching rule B. Compared with the engagement scheme in which the torque exchange overlap time for both sets of clutches is 0.3 s, the scheme with a torque exchange overlap time of 0.15 s indicated a shifting time increase of 0.2 s, a slip energy increase of 4%, and a minimum output torque of the transmission increase of 2%. In the scheme with a torque exchange overlap time of 0 s, the shifting time increased by 0.15 s, the slip energy decreased by 13.5%, and the minimum output torque of the transmission decreased by 17%. Through the study of shifting performance under three different clutch engagement patterns, it is concluded that, during the shift from forward gear II to gear III in the YTO TX4A transmission system, appropriately reducing the torque exchange overlap time for both sets of clutches and avoiding simultaneous torque exchange can reduce the complexity of clutch control. This leads to smoother, more powerful, and more comfortable power shifting, effectively prolonging the service life of the transmission system.