Sir Francis Drake's attack on Saint Augustine on May 28 and 29, 1586. Engraving by Baptista Boazio. The raid on St. Augustine was a military event during the Anglo-Spanish War in which the Spanish settlement of St. Augustine was captured in a small fight and burnt by an English expedition fleet led by Francis Drake. This was part of Francis Drake's Great Expedition and was the last engagement on the Spanish main before Drake headed north for the Roanoke Colony. The expedition also forced the Spanish to abandon any settlements and forts in present-day South Carolina.