Background: Investment in disaster risk reduction is crucial in order to mitigate disaster damage. However, for many countries, particularly developing ones, financing investment in disaster risk reduction is challenging. This study aims to examine the factors that affect investments in flood protection and the approaches to securing investments by analyzing investment trends in Japan. Methods: This study examines 150 years of flood protection and investment cycles that helped reduce damages in Japan. The dataset of flood protection budgets, flood damage, and national income since 1878 was created from public statistics. Documents and reports concerned with disaster management, river management, and finance were examined. Results: The study found five investment cycles of flood protection from the late 19th century to the present. The country established financing mechanisms, such as legislation and long-term plans, following major flood disasters. However, external shocks such as war, economic recession, disaster, and tightened national finance had a major impact on these investments. The fluctuations in the budget created an investment cycle. The country had increased its budget to 0.9% of its national income in the 1990s. It often experienced flood damage accounting for over 1% of the national income until 1961, but succeeded in decreasing the damage to less than 1%, and currently it is limited to less than 0.4%. Conclusions: The financial mechanisms established from the long-term perspective could support an increase in budgets for flood protection, leading to a decrease in damage. However, established financing mechanisms may weaken the financial flexibility of the country.