Battle of Pinos The Battle of Pinos was a naval engagement between a Spanish fleet under Admiral Bernardino Delgadillo y Avellaneda and the surviving ships of Francis Drake ' s expedition to the Spanish West Indies , now in command of Drake ' s lieutenant , Sir Thomas Baskerville , which took place off the Island of Pinos during the Anglo - Spanish war of 1585 . The Spanish squadron was victorious , capturing two English ships . Background . After failed attacks against San Juan de Puerto Rico and Panamá , during which Francis Drake and John Hawkins had perished from dysentery , the English fleet anchored in Portobello to reorganize and careen their ships prior to return to England . Sir Thomas Baskerville , Colonel - General of the landing forces , was then elected by his officers as the new commander of the retreating fleet , whose number of ships soon decreased to 18 , as two of them , the " Delight " and the " Elizabeth " , had to be burned or sunk due to lack of crew . Two generals , 15 captains and 22 officers had died in combat or from disease ; a loss which demoralized the men on board . The English fleet departed Portobello on February 8 . A few days later a storm scattered the fleet . Several ships returned to England via Jamaica , while Baskerville , with the bulk of the fleet , headed to Cabo Corrientes to sail to his country along the northern coast of Cuba . In Spain , meanwhile , news of Drake - Hawkin ' s attack in Gran Canaria had reached the Spanish court . A fleet of 8 galleons and 13 other vessels ( mainly hulk s and pinnaces ) under Captain General Don Bernardino de Avellaneda , with Juan Gutiérrez de Garibay as Admiral , Juan de Villaviciosa as flag captain , and about 3 , 000 men aboard , was dispatched from Sevilla to Cuba , which was supposed to be menaced by the English . In early March they arrived at Cartagena de Indias , disposed to pursue Baskerville . Battle . On March 7 , part of Avellaneda ' s fleet surprised two English ships south of Cienfuegos . They were the " Pegasine " and were commanded by Thomas Maynarde . Engaged by the Spaniards , they received extensive damage , but finally managed to escape avoiding the dangerous shoals of Pinar del Río , and reached England on May 3 , just a week before Avellaneda encountered the bulk of the English fleet supplying of wood and water at Guaniguanicos Cove , in the Island of Pinos , south of Cuba . Avellaneda immediately ordered his ships hoist their flags and attack . Baskerville , whose flagship was John Hawkin ' s " La Garlande " , however , tried to avoid combat scattering his ships towards Cape San Antonio . Most of the English ships escaped because they abandoned their boats and threw their baggage into the water . Vice Admiral Juan Gutiérrez de Garibay ' s three - ship vanguard managed to intercept and capture two ships : a 300 - man galleon and a 25 - man patache whose prisoners were put to work on Havana ' s fortifications . The loss on the Spanish side amounted to 80 men killed or wounded and a warship , sunk during the clash . Aftermath . Avellaneda ' s fleet pursued the English as far as the Old Bahama Channel . On 22 May , returning to Havana , they captured John Crosse ’ s pinnace " Little Exchange " off the town . This was not the last loss suffered by the English , as only 8 of the 28 warships which had departed England on 1595 returned to their country . The survivors reached Plymouth at the same time the Spanish treasure fleet disembarked at Sanlúcar de Barrameda with 20 million silver dollars , one of the largest shipments ever to arrive from the Americas .