This chapter approaches the beginning of the seventeenth-century Portuguese–Dutch War in Asia in light of the discussion on the military revolution. More specifically, it focuses on the much-debated issue of whether a military revolution in Europe produced a European military exceptionalism that made Europeans militarily superior to non-Europeans in the early modern period. For this purpose, the chapter examines case studies of three great but unsuccessful Portuguese expeditions against the Dutch dispatched to Southeast Asia between 1597 and 1606. An important historiographical tradition has assumed that Asian military influence on the Portuguese in Asia during the sixteenth century made the Portuguese militarily inferior to European enemies such as the Dutch in the seventeenth century. The chapter, however, argues against the idea that the expeditions failed because the Portuguese were only too well adjusted to an Asian military context and therefore ill prepared to face the European novelty represented by the Dutch. The important contribution of the Asian allies of the Dutch to the Portuguese defeats is a central point in the chapter’s argument.