Battle of Flores ( 1591 ) The Battle of Flores was a naval engagement of the Anglo - Spanish War of 1585 fought off the Island of Flores between an English fleet of 22 ships under Lord Thomas Howard and a Spanish fleet of 63 ships under Alonso de Bazán . Sent to the Azores to capture the annual Spanish treasure convoy , when a stronger Spanish fleet appeared off Flores , Howard ordered his ships to flee to the north , saving all of them except the galleon " Revenge " , which , surprised by a second squadron of Spaniards , was cut off from the rest of the fleet . After a fight which lasted until the night , " Revenge " , out of action , surrendered . Background . In order to impede a Spanish naval recovery after the Armada , Sir John Hawkins proposed a blockade of the supply of treasure being acquired from the Spanish Empire in the Americas by a constant naval patrol designed to intercept Spanish ships . " Revenge " was on such a patrol in the summer of 1591 under the command of Sir Richard Grenville . The Spanish , meanwhile , had dispatched a fleet of some 55 ships under Alonso de Bazán , having under his orders Generals Martín de Bertendona and Marcos de Aramburu . Bazán learned that the English were patrolling around the northern Azores . In late August 1591 , having been joined by 8 Portuguese flyboat s under Luis Coutinho , the Spanish fleet came upon the English . Howard ' s fleet was caught while undergoing repairs and when the crews , many of whom were suffering an epidemic of fever , were resting ashore . Battle . Bazán tried to surprise the English fleet at anchor , but Sancho Pardo ' s Vice - flagship lost their bowsprit , forcing the attack to be delayed . It was not until 5 PM when Bazán ' s ships bore down the channel which separated Flores and Corvo islands . Howard , alerted to the arrival of the Spanish , managed to slip away to sea . An exchange of fire took place between both fleets before they became separated . Grenville , however , preferred to fight and went straight through the Spaniards , who were approaching from the eastward . Meanwhile " Defiance " , Howard ' s flagship , received heavy gunfire from Aramburu ' s " San Cristóbal " before withdrawing from the battle . " Revenge " was left behind and directly engaged by Claudio de Viamonte ' s " San Felipe " . Viamonte boarded the English galleon , suffering the misfortune of the grappling hook parting after having only passed 10 men aboard her . Shortly after Martín de Bertendona ' s " San Bernabé " did the same , this time successfully , and managed to rescue seven survivors of " San Felipe " ´s boarding party . " San Bernabé " ´s grappling was decisive to the fate of " Revenge " , because the English warship lost the advantage of her long - range naval guns . Conversely , the heavy musket ry fire of the Spanish infantry forced the English gunners to abandon their post in order to repulse the attack . At dusk , having dispersed the bulk of the English fleet , " San Cristobal " rammed " Revenge " underneath its aft - castle , putting on board of the English ship a second boarding party which captured her colours . The Spanish soldiers got as far forward as far as the mainmast before being forced to retreat due to the heavy musketry fire made from the aftcastle . " San Cristóbal ' s " bow had been shattered by the ramming and she had to ask for reinforcements . Antonio Manrique ' s " Asunción " and Luis Coutinho ' s flyboat " La Serena " attacked then at the same time , increasing the number of ships beating the " Revenge " to five , which was still grappled by the galleons " San Bernabé " and the damaged " San Cristóbal " . Grenville held them back with cannon and musket fire until , being himself badly injured and " Revenge " severely damaged , completely dis - masted and with 150 men killed or unable to fight , surrendered . During the night Manrique ' s and Coutinho ' s ships sunk after they collided with each other . Aftermath . Despite the damage Grenville had inflicted , the Spanish treated " Revenge ' s " survivors honourably . Grenville , who had been taken aboard Bazán ' s flagship , died two days later . The Spanish Treasure Fleet rendezvoused with Bazán soon after , and the combined fleet sailed to Spain . They were overtaken by a week - long storm during which " Revenge " and 15 Spanish warships and merchant vessels were lost . " Revenge " sank with her mixed prize - crew of 70 Spaniards and English prisoners near the island of Terceira , at the approximate position . The battle , however , marked the resurgence of Spanish naval power and proved that the English chances of catching and defeating a well - defended treasure fleet were remote . It also hinted at what might have happened in Gravelines in 1588 if Medina Sidonia had succeeded in luring the English ships within grappling range of the Armada , and if the cannonballs had actually fit the Spanish cannon ( they ' d been manufactured in different areas of the Spanish Hapsburg Empire and so were not all designed in the same way , shape or size ) .