Contestation is a phenomenon from the impact of urbanization process in heritage sites. It is often highly politicized, and almost always has caused conflict among community, private sectors and government entities. They conflicted to decide their own priorities for development of their place and environment. The social consequences associated with the limitation of urban development plan enforcement. It is also criticized for causing environmental degradation, intensifying segregation, and undermining the vitality of existing urban areas. It is also frequently attacked on aesthetic grounds. It has a direct impact to cultural heritage sites too. It is needed a description of the impact as sell as the problems and consequences of the urban sprawl in Trowulan. It takes the view that a critical understanding of changes in dynamic urban growth is crucial for developing strategies for a heritage sites management and its protection for heritage sites, including matters relating to legal issues, area-based management in heritage sites and control mechanism. This paper aimed to introduce the procedure on how to identify any contestation appears in case of heritage site versus new urban development.