Anglo-Spanish War: After a 15-day siege Spanish troops in San Juan, modern-day Puerto Rico, surrendered to an English force under Sir George Clifford.

The Anglo-Spanish War (1585–1604) was an intermittent conflict between the Habsburg Kingdom of Spain and the Kingdom of England that was never formally declared. It began with England's military expedition in 1585 to what was then the Spanish Netherlands under the command of Robert Dudley, Earl of Leicester, in support of the Dutch rebellion against Spanish Habsburg rule.

The Battle of San Juan was a military and naval action on June 15, 1598 when an English force of 20 ships and 1,700 men under Sir George Clifford, Earl of Cumberland, overwhelmed and took the Spanish fortress Castillo San Felipe del Morro and thus took the city of San Juan, Puerto Rico. They were able to hold the castle for 65 days but disease took its toll and the English forces left, but not before sacking and burning San Juan to the ground. This was the only attack that broke through and captured El Morro castle.

Sir George Clifford, 3rd Earl of Cumberland, 13th Baron de Clifford, 13th Lord of Skipton, was an English peer, naval commander, and courtier of Queen Elizabeth I of England. He was notable at court for his jousting, at the Accession Day Tilts, which were highlights of the year at court. Two famous survivals, his portrait miniature by Nicholas Hilliard and a garniture of Greenwich armour, reflect this important part of his life. In contrast, he neglected his estates in the far north of England and left a long succession dispute between his heirs.