(1) Background: Being underweight is a known risk factor for hip fractures. However, it is unclear whether the cumulative underweight burden affects the incidence of hip fractures. Therefore, we explored the effect of the cumulative underweight burden on the development of hip fractures; (2) Methods: In a cohort of adults aged 40 years and older, 561,779 participants who were not underweight and had no hip fractures from 2007 to 2009 were identified. The risk of hip fracture from the time of the last examination to December 2018 according to the cumulative burden of being underweight (based on 0 to 3 examinations) was prospectively analyzed; (3) Results: During follow-up (mean 8.3 ± 0.8 years), the prevalence of newly diagnosed hip fractures was 0.2%, 0.4%, 0.5%, and 0.9% among those with 0, 1, 2, and 3 cumulative underweight, respectively. The adjusted hazard ratios (HRs) with 95% confidence intervals (CIs) of groups meeting the diagnostic criteria for underweight 1, 2, and 3 compared to 0 were 2.3 (1.6–3.3), 2.9 (1.8–4.5), and 4.5 (3.4–6.1), respectively (p for trend < 0.01); (4) Conclusions: The risk of hip fracture increased as the burden of underweight accumulated.