This paper examines the flood situation of the Yoshino River in the Meiji era. Using water level records and lateral profile of the river of those days, a numerical simulation was performed for the flood in Meiji 44, and it was compared with the situation of the flood damage described by the newspaper articles. The flood actual condition in Meiji 44 was investigated in general by the numerical analysis. In the Yoshino River of the time where maintenance of a river bank etc. was not progressing, it turned out that the flood often occurred and it had suffered the serious damage in which many bridges and houses were washed away. As mentioned above, by clarifying the situation of the past flood, when considering future flood control plan, it becomes precious data.