Battle of the Strait of Gibraltar ( 1591 ) The Battle of the Strait of Gibraltar was a naval action off Gibraltar on 24 April 1591 . A fleet of three English merchant vessels escorted by a larger armed merchant vessel " Centurion " was attacked by five Spanish galley s . Ultimately , the Spanish were repelled , but not before the English vessel " Dolphin " was sunk by one of the galleys . Background . The merchants of London , which included ships of the Levant Company , were sailing for various ports but had banded together to sail through the heavily Spanish - dominated Straits of Gibraltar . Among these ships was the " Centurion " , a large armed merchant vessel but weakly manned . The " Centurion " arrived at Marseilles , on her outward bound voyage after delivering her goods , she remained there for more than five weeks , taking in lading , and then intended to return to England . When she was ready to depart from Marseilles , there were other smaller sundry ships . Their masters of which interested Robert Bradshaw of Limehouse , the master of the " Centurion " , to stay a day or two for them until they could get in readiness to depart . They agreed that it would be far better for them all to go in company for mutual support and defence , than to run the hazard of falling into the hands of the Spanish galleys in the Straits as they had done the year before . Bradshaw agreed and set out along with them all engaging mutually to stand by each other , if they chanced to fall in with any of the Spanish galleys . The Spanish meanwhile had sent six galleys from Cartagena , part of a squadron of twelve under Giovanni Andrea Doria , to convey the Spanish ambassador to Rome . Action . Sailing altogether along the coast of Spain , they were suddenly becalmed upon 24 April in the Straits of Gibraltar , where they immediately saw the six galleys making towards them . " Centurion " was prepared for any such engagement , having prepared their close quarters in readiness . However , there were only 48 men and boys fit for duty . As the Spanish galleys bore up , the " Centurion " discharged her ordnance . The other merchant vessels initially lay out of danger , while five of the galleys laid on board the " Centurion " , which they made themselves fast with their grappling irons , two to a side with a fifth galley on the stern . On both sides of the ship the Spanish were repelled ; the ropes and grapples were cut successively and fire was maintained to cripple the Spanish ships . The " Centurion " was set ablaze several times , but was extinguished each time with little damage . In every one of these five galleys there were about 200 soldiers ; who battered the " Centurion " and shot her mainmast through . In the end , however , the Spaniards had almost spent their ammunition , so that they were obliged to load with hammers and the chains of their galley - slaves . At length , the Spaniards were constrained to unfasten their grapplings and shear off as they had suffered heavy casualties and many of their ships were severely damaged . Meanwhile , the smaller and less armed " Dolphin " was engaged by one of the galleys and eventually blew up , either by enemy gunfire or scuttled by their own crew . There were no survivors , including " Dolphin " ´s captain , John Giles . Aftermath . The action had lasted for five and a half hours . By the end , both English and Spanish were glad to draw off , and the Spaniards did not renew the fight . The Spanish had suffered many casualties many of whom drowned ; in the region of around 200 men . The " Centurion " had four men killed and another ten men injured severely . Next day six other Spanish galleys came and kept watch on the Centurion but did not attempt any kind of action . The rest of the convoy managed to arrive in London without further incident , although the sinking of the " Dolphin " resulted in the loss of £2 , 000 . The " Centurion " would play apart in the Capture of Cadiz in 1596 and then taking part in the capture of San Juan in 1598 .