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Background: Cardiovascular-disease (CVD) is the leading cause of death, and the association between obesity and CVD is particularly significant among women. Given the evidence highlighting the significance of weight-gain velosity, we aimed to elucidate its influence on cardio-ankle vascular index (CAVI), a reliable surrogate marker of CVD, and identify the high-benefit population where this influence is most pronounced. Methods: This multicenter retrospective study used electronic data from annual health checkups for workers in Japan. Individuals who voluntarily measured CAVI in 2019 were included, and weight-gain velosity was defined as the mean BMI gain from 2015 to 2019. Our primary outcome was the relationship between weight-gain velosity and CAVI. Results: Among 459 individuals, 53 had CAVI ≥ 9. Random forest analysis revealed that age was the most important factor, followed by lipid metabolism, weight-gain velosity, and glucose metabolism, with sex being the least important. Non-linear regression analysis of the effect of age on CAVI ≥ 9 showed the effect was pronounced after age 60, and the trend was greater in women. Among individuals aged 60 or younger, the aOR of weight-gain velosity for CAVI ≥ 9 was significantly positive (aOR 11.95, 95 %CI 1.13–126.27), while it was not significant for those older than 60. The relationship between weight-gain velosity and CAVI provides a new perspective on CVD risk factors. The effects of age, especially after 60, and weight-gain velosity in early- to middle-adulthood on arterial stiffness are emphasized. Conclusions: These findings underscore the importance of weight management under age 60, especially in women.