While the study of urban historical traditions in the architectural curriculum is a shared mandate, its modes of instruction have scarcely moved beyond the usual stock of precedent studies focused on form, style and typology. This method of instruction, though sufficiently providing parallel background knowledge for students of architecture, further isolates the disciplines of history, theory and criticism as increasingly remote parameters for design. In the context of Asian architecture's ever more prolific expansion, such antiquated and rarefied notions of history need to be urgently reviewed. Indeed, the future of Asian space hinges on the premise that its globalized formats are held in equilibrium by critical knowledge of its localized historical origins and impetus. This chapter thus proposes a more complex relationship between history and design by revisiting how the historical aspects of "site" may be activated in the academic design studio through experimental pedagogies focused on the representations and fabrications of architectural histories conducted in relation to particular sites. Drawing on "Site, Situation, and Spectator," an interdisciplinary site-responsive program developed at the National University of Singapore, new methodologies for appraising and intervening with, as well as subsequently representing, histories of urban sites will be examined. In the island state of Singapore, the rapidly changing patterns of reoccupied, reclaimed, redeveloped and contested sites in its built environment become causes of concern in terms of their cultural and historical sustainability. The question of what constitutes a "site" in the academic context can be prosaic. Yet, given Asian architecture's expansion, this question has never been more urgent. This chapter discusses an expanded notion of site by borrowing and transforming art historical principles, so that these ideas become relevant for architectural production. The challenge is to find new means of engaging future changes while maintaining a critical engagement with a site's historical lineage. Techniques are adopted from within architecture and its allied disciplines - Art history, cultural geography and material culture - so that the design process, which begins with a revision of attitudes toward the site's history, may cultivate broader contexts beyond a typical focus on precedence. In particular, the chapter will discuss how an expanded notion of "site" enables different modes of representation and fabrication, which ultimately poses history as a constructed and ever-changing category, aligned with the vicissitudes of Singapore's and Asia's future space.