Battle of San Juan (1598)

Part of the Anglo-Spanish War (1585–1604)

Aerial view of Old San Juan

Date	June 15–30, 1598
Location	Castillo San Felipe del Morro (present-day Puerto Rico)
Result	English victory

Belligerents

Spain

Kingdom of England

Commanders and leaders

Antonio de Mosquera

Sir George Clifford

Strength

350 soldiers and militia

20 ships,
1,700 men

Casualties and losses

250 surrendered
50 casualties
2 ships captured

60 killed,
40 other deaths

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 plundering and burning San Juan to the ground. It was this attack that proved to be the only one to ever break through and capture El Morro castle.

Sir Francis Drake had been defeated in 1595 and the report alarmed Elizabeth I that she wanted to avenge or 'dirten' the defeat. Queen Elizabeth almost immediately sent a new expedition led by the third Earl of Cumberland, Sir George Clifford, so that he could seize San Juan and hold as long as possible.

Merely three years after Drake's attack, Cumberland arrived off Dominica with his 600-ton ﬂagship Malice Scourge captained by John Watts, plus the 400-ton vice-ﬂagships Merchant Royal of Sir John Berkeley and Ascension the 400-ton merchantman Alcedo, and Prosperous, 300-ton Centurion of Henry Palmer, Consent, and Sampson of Henry Clifford; 250-ton galleon Constance of Hercules Fulham; 210-ton Guyana 200-ton Margaret and John; 190-ton Royal Defence; 120-ton Affection of William Fleming, and Anthony 80-ton Pegasus the frigate Discovery, the pinnace Scout, the bark Ley; plus two unnamed barks. In total the fleet consisted of 1,700 men and twenty ships. After refreshing his ﬂeet for nearly a week, the Earl transferred to the Virgin Islands on 11 June and celebrated a ﬁnal muster three days later before laying in a course for San Juan.

On the morning of 16 June, Cumberland disembarked 700 men at Cangrejos Bay twelve miles east of San Juan, then marched until nightfall. However one mile short of the city he and his men came up to a bridge known as San Antonio, the only land access to the San Juan islet. This was held by around 100 Spanish soldiers. They managed to repel the English assault who inflicted forty casualties, while the Earl of Cumberland himself almost drowned trying to cross the San Antonio channel. The Spaniards suffered only four casualties. Next morning, the English use their boats to outﬂank the Spanish position, disembarking at Escambrón Point while bombarding Boquerón Redoubt (called Red Fort by the English). The fort was bombarded into submission and the guns silenced with ease as the English deliberately grounded one of their ships in front of the fort which enabled point blank precision firing; by the evening most of the defenders had retreated. The English took possession of the area and consolidated while the rest of the force arrived; two Spanish vessels were seized as a result.

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Wikipedia