Compression bandages are subjected to a repeated and prolonged spatial deformation, at knee and ankle positions, during ambulatory conditions of the lower limb. The important dynamic variables like speed, the amount of the degree of bending at knees and ankles, etc. could affect the long-term compression behavior of the bandage. The aim of this study was to investigate the dynamic behavior of medical compression bandage using a newly designed dynamic leg-segment model. A prototype was especially designed to simulate the dynamic behavior of the human leg using a mannequin limb. The influence of major factors, i.e. the speed of the reciprocating movement of the mannequin, the amount of displacement amplitude of the reciprocating movement of the mannequin (i.e. step size), and the applied extension level given to the bandage, on the sub-bandage pressure exerted by the bandage on the mannequin surface were analyzed using this model. It was observed that the rate and amount of the sub-bandage pressure drop increased under dynamic mode of the mannequin as compared to static mode. A higher drop in the sub-bandage pressure under dynamic mode was obtained with increasing the amount of displacement amplitude of the mannequin leg and also with increasing the applied extension level given to the bandage. The ambulatory conditions of the leg result in cyclic deformations in the wrapped bandage, and this influences the sub-bandage pressure variations over time. The proposed leg-segment model enables to assess dynamic behavior of different compression bandages under customized conditions and hence could be used for comparing and pre-evaluating different bandage products.