The Battle of Guadalupe Island, also known as the Battle of Guadalupe, was a naval action that took place off Guadalupe Island, Caribbean Sea, on 8 November 1595, between a Spanish force of five frigates commanded by Don Pedro Tello de Guzmán and Don Gonzalo Méndez de Cancio, and an English squadron of nine ships, during the unsuccessful English military expedition of 1595 against Spain and their possessions, led by Sir Francis Drake himself, Sir John Hawkins and Sir Thomas Baskerville, as the context of the Anglo-Spanish War (1585–1604). The result was a Spanish victory.