This dissertation uses the analytical tool of “competing visions” to examine the historical development of China’s Inner Asian highland from 1368 to 1600. Straddling the Chinese heartland, Tibetan plateau, and the Mongol steppe, the highland region was a convergence zone that facilitated a constant flow of people, goods, and knowledge. Competing visions over the highland, as both historical phenomena and research perspective, highlight the dynamic nature of the region and its function as a bridge for cross-cultural encounters and transregional geopolitical interactions. By investigating how and why different social groups understood the highland differently, this dissertation scrutinizes the operating mechanism of a borderland society and its role in macroregional geopolitics. Focusing on material exchanges, knowledge circulations, border-crossings, and contestations over territoriality through the lens of Ming emperors, highland regime lords, Tibetan Buddhist monks, Ming military deserters, and Mongol nomads, this dissertation highlights the formation of a borderland space as the outcome of constant compromise and negotiation. This dissertation argues that the conflict of ideas and agendas in the highland provided the driving force not only for the formation of its political-economic landscape, social structure, and human-environment relations, but also the transformation of the highland from a middle ground where multiple territorial perceptions co-existed into a demarcating frontier between Ming China and the Inner Asian world.