Middle-aged individuals may not respond in a similar manner as younger individuals. The study’s objective was to examine the effect of static (SS) and dynamic stretching (DS) in young and middle-aged men on subsequent performance. Ten young (22 ± 1.4 years) and 8 middle-aged men (46.3 ± 6.5 years) participated in 3 conditions consisting of SS (4 × 30 s for right and left quadriceps, hamstrings, and plantar flexors), DS (8 × 30 s of bilateral butt kicks, walking lunges, and plantar flexors) and control. Dependent variables included sit and reach, hip extension flexibility, countermovement jump (CMJ) height, drop jump (DJ) height, static balance, reaction (RT) and movement time (MT). Measurements were taken pre-intervention, post- and 10 min post-intervention. A 3-way repeated measurement ANOVA revealed that the younger men had higher jump heights, faster RT and MT, and greater flexibility than the middle-aged men. DS significantly enhanced DJ (p = 0.04) and CMJ (p = 0.006) height compared with SS and control conditions. SS (p < 0.0001) and DS (p = 0.004) post-intervention sit and reach scores were significantly greater than pre-intervention scores. There were no significant differences between the SS and DS sit and reach scores. CMJ heights were impaired (p = 0.04) by SS. Conversely, DS post-intervention jump heights were significantly (p < 0.0001) higher than SS post-, control post-, and control 10 min post-intervention. SS-induced impairments and DS-induced enhancements of CMJ height were not affected by age. DS provided similar improvements in sit and reach scores as SS. DS is recommended as the most appropriate stretching routine prior to work or athletic performance for younger and middle-aged men.