This examination of the earliest Spanish-Amerindian encounters on Hispaniola and in Tierra Firme adopts a historical perspective on indigenous warfare. A chronological timeline monitors the recorded encounters and hostilities between the native Amerindian societies and the Spaniards from Columbus’s 1492 voyage until the destruction of the first permanent Spanish settlement of Santa María de la Antigua del Darién in 1524. The timeline evaluates the proposition that Amerindian societies intensified their warfare practices in response to European incursions. The available information about the size, composition, preparedness, and organization of the native forces is juxtaposed against that of the Spanish forces. The warfare strategies and tactics are examined, both offensive and defensive measures, as well as the actions of the opposing forces in the aftermath of a confrontation. The findings do not support the proposition that Amerindian warfare practices changed significantly in the face of European incursions. The study concludes with a consideration of the unexpected innovations and consequences of the military encounters between late fifteenth- and early sixteenth-century Europeans and Amerindian chiefdoms.