Passive stretching is commonly recommended to help reduce passive stiffness in older adults, yet their acute viscoelastic stretch responses are still unclear. The purpose of this study was to determine the influence of age on the acute viscoelastic responses to a practical stretching intervention. Twenty-two younger (24 ± 3 years) and 14 older (67 ± 3 years) males performed four 30-second passive stretches of the plantar flexors at a predetermined torque threshold. The absolute and relative change in stress relaxation (decline in torque during each 30-second stretch) and creep (increase in ankle joint angle across the 4 stretches) were recorded. Passive stiffness was calculated as the slope of the angle-torque curve at 10° angle of dorsiflexion. There were no differences for the absolute stress relaxation responses (p ≥ 0.118); however, the relative change in stress relaxation was greater (p = 0.010) for the younger vs. older men at stretch 1 (13.0 vs. 8.6%) and decreased across stretches for the younger men (stretch 1 > 3 and 4; p ≤ 0.018), whereas the older men demonstrated a similar relative change across all 4 stretches (p = 0.917). No age related differences were found for either the absolute or relative creep responses (p ≥ 0.072). Passive stiffness was also greater in the older men (p = 0.044). These results suggest that the younger men displayed a greater initial relative stress relaxation response that diminished across the repeated stretches, whereas the older men experienced a smaller relative response that remained constant across the four 30-second stretches. However, the increase in range of motion for a given stretch torque (creep) across all 4 stretches was similar between groups despite differences in passive stiffness.