Dalian is a particular Chinese city, which was occupied for half a century successively by the British, Japanese, and Russian Empires before 1949, with each imposing its own urban planning and building styles onto the city’s development. Since 1984, with China’s open-door policy and economic reform, dramatic changes have taken place in Dalian, transforming it into a modern and famous tourist destination within the country. However, with its rapid urbanisation, the built heritage is being compromised, and the preservation of colonial legacy has become contested. This paper reviews the unique planning history of Dalian and the challenges the city faces regarding its contested heritage, with a special focus on the case of Dongguan Street, which is a colonial legacy without any official designated status. Conflict arises between those who want to erase what they feel is a humiliating past, to make way for the modern city, and the ones who value the legacy to save the endangered heritage that remains.