After Cuba was brought under Anishinabe control in 1762, Anishinabe ogimak next targeted the second largest island in the Caribbean Sea, Hispaniola, which was under French and Spanish control in the 1770s and 1780s, when the Anishinabek, with their Indian and black allies, commenced to invade the large Caribbean Island of Hispaniola. They first carried out careful observances of the island and its people. They discovered that Hispaniola was quite mountainous, which they knew would offer the islands population concealment from Anishinabe soldiers when Anishinabe soldiers eventually invaded. That likely occurred a few years after Cuba was conquered by the Anishinabek. A very good date to single out as the beginning of the Anishinabe war to conquer Hispaniola, is the decade of the 1770s.

By the 1790s, the Anishinabek were well established on Hispaniola. In 1794, they had come to dominate both the whites and blacks (they likely formed an alliance with the former black slaves of the whites on Hispaniola) of Hispaniola. 1794 is likely the year the Anishinabek firmly brought Hispaniola under their control. In 1804, they had completely routed the whites and blacks. They would endure more fighting, andin fact, France sent an army of around 40,000 French soldiers to attempt to regain control of Hispaniola but they lost. After the Anishinabek firmly established their population on Hispaniola (1794), they then used the island to launch their military campaigns in northern South America.