This study compared the effects of static stretching (ST) and repeated muscle contractions (CON) on the viscoelastic properties of tendon structures in vivo. Eight male subjects performed ST (passively flexed to 35 of dorsiflexion) for 5 min and 50 repetitions of isometric maximum voluntary contraction (MVC) for 3 s each with 3 s relaxation. Before and after each task, the elongation of the tendon and aponeurosis of the medial gastrocnemius muscle (MG) was directly measured by ultrasonography, while the subjects performed ramp isometric plantar flexion up to MVC, followed by a ramp relaxation. The relationship between the estimated muscle force (Fm) and tendon elongation (L) during the ascending phase was applied to a linear regression, the slope of which was defined as stiffness of the tendon structures. The percentage of the area within the Fm-L loop to the area beneath the curve during the ascending phase was calculated as an index representing hysteresis. The ST protocol significantly decreased the stiffness (-8%) and hysteresis (29%)., respectively. In contrast, the CON protocol significantly decreased the stiffness, but not the hysteresis. These results suggested that the stretching and repeated contractions would make the tendon structures more complaint, and further decreased the hysteresis of the tendon structures.