The Battle of San Juan (1595) was a Spanish victory during the Anglo–Spanish War. This war broke out in 1585 and was fought not only in the European theatre but in Spain's American colonies. After emerging from six years of disgrace following the resounding defeat of the English Armada at Lisbon in 1589, Francis Drake embarked on a long and disastrous campaign against the Spanish Main, suffering several consecutive defeats there. On 22 November 1595 Drake and John Hawkins tried to invade San Juan, Puerto Rico with 27 ships and 2,500 men. After failing to be able to land at the Ensenada del Escambron on the eastern end of San Juan Islet, he attempted to sail into San Juan Bay with the intention of sacking the city. Unable to capture the island, following the death of his comrade, John Hawki