Age is an important factor that dictates bamboo’s mechanical properties. In Japan, bamboo plants aged 3–5 years are selected for use as materials because of their robustness and decorative or craft-friendly characteristics. In this study, the age-dependent and radial sectional differences in bamboo’s dynamic viscoelastic properties in relation to lignin structural variation, were evaluated. We used Phyllostachys pubescens samples at the current year and at 1.5, 3.5, 6.5, 9.5, 12.5, and 15.5 years of age. There was a clear age dependence in the peak temperature of tan δ and in the yield of thioacidolysis products derived from β-O-4 lignin structures. The highest peak temperature tan δ value was detected in 3.5-year-old bamboo, which contained the highest amount of the thioacidolysis products. Moreover, tan δ’s peak temperature was always higher on the outer side, and the ratio of S/G thioacidolysis products was always higher on the inner side of bamboo plants of all ages. These results suggest that changes in bamboo’s thermal softening properties from aging are caused by the maturation and degradation of lignin in bamboo.