In the process of urban transformation, constructing the urban axis through urban planning is one of the important features for the government to transform a city. During the Japanese colonial period, the Office of the Governor-General modeled the experience of urban reform in western advanced countries, outlined the new structure of Tainan City with urban plans, and built a new urban axis to infused development momentum into the traditional city. Previous studies often dealt with the urban transportation network rather than the changes of the urban axis when analyzed the urban development during the Japanese rule. Based on an analysis of the implications of the old and new axes in Tainan City, this study explores the strategy of replacing Tainan’s old commercial axis with a new urban axis by a series of railways, highways, and waterways during the Japanese colonial period. It was also based on the goals related to Japan’s modernized urban transformation policies, which demonstrate the governing ability of the Office of the Governor-General and the legitimacy of colonial rule. This study found that Tainan’s new urban axis is a key consideration to introduce a modern Western urban design technique in Tainan, which has considerable enlightenment for subsequent urban construction and landscape control.