Battle of Santiago de Cuba ( 1748 ) The 2nd battle of Santiago de Cuba , which took place on April 9 of 1748 , was a failed attempt by elements of the British Royal Navy under Rear - Admiral Charles Knowles to force the entrance of the port of Santiago de Cuba with the aim of striking a blow to the Spanish trade and privateering , since Santiago was a major base of the Spanish privateers in the Caribbean . Two British ships of line were put out of action by the batteries of Morro Castle and had to be towed to open sea . The remaining British warships retreated soon after . Background . Sir Charles Knowles , who had been promoted to rear - admiral of the white on 15 July 1747 , and appointed as commander in chief on the Jamaica station , prepared in 1748 an expedition with the aim of recover from the setbacks suffered during the previous stages of the war by attacking the Spanish trade and protecting their own . On 17 February he departed Port Royal with 240 of Governor Trelawney ’ s Jamaican troops aboard his 80 - gun flagship " HMS Cornwall " , 60 - gun " HMS Plymouth " , 70 - gun " HMS Elizabeth " , 58 - gun " HMS Canterbury " , 60 - gun " HMS Strafford " , 60 - gun " HMS Warwick " , 60 - gun " HMS Worcester " , 50 - gun " HMS Oxford " , and the 16 - gun , 100 - man sloops " Merlin " and " Weazel " . He had initially intended to take his squadron and attack Santiago de Cuba , but contrary winds led to him deciding instead to attack Fort Saint Louis de Sud . He arrived on 8 March 1748 , and after subjecting the fort to a heavy bombardment forced its surrender . Attacks on Petit Guave and Cap François , however , had to be postponed due to lack of troops . It was therefore decided to proceed with the attack upon Santiago . Battle . The afternoon of 28 March , having been joined by " HMS Lenox " and the frigates " Vainqueur " , " Vulture " , and the tender " Sharp " , the British squadron arrived in sight of the Cuban coast . Its battle line was as follow : " Plymouth " , " Cornwall " , " Canterbury " ( flagship ) , " Elizabeth " , " Strafford " , " Warwick " , " Worcester " , " Lenox " , " Vainqueur " in the van , " Vulture " abreast the flagship , and " Sharp " abreast the rear . Captain Dent ’ s " Plymouth " , who had been detached to reconnoite Santiago ’ s entrance , noticed that it was not difficult . Faint winds , however , prevented Knowles to attack , forcing the squadron to lay off for the night within view of the Spaniards . The governor , Brig . Gen . Arcos Moreno , immediately ordered a ship of about 200 tons warped out of the inner bay to support a 10 - inch hawser stretched from shore to shore , partially blocking the entrance . The probability of meeting with obstructions in the mouth has been taken into consideration , and a Spanish pilot had been brought aboard the British fleet to help to carry the British ships into the harbour . Dent , whose " Plymouth " has been selected to lead the attack , was ordered to shoot the pilot or throw him overboard if he raised any objetcions . " Canterbury " was decided to be anchored off the end of the Apostle ' s battery to help the leading ships by shelling the Spanish fortications with a 10´´ mortar taken at Fort Louis and mounted upon her quarter deck . The flag was then hoisted aboard the " Worcester " , and when the sea breeze came in , was given the order to attack . The squadron stood in a breeze at S . E . , giving it about four knots . " Canterbury " opened fire on the Mora as soon as he came within range . " Plymouth " , meanwhile , found a defensive chain across the harbour . Captain Dent sent the long boats and barges to clear the obstacle . His ship , however , came under fire from the Spanish batteries and was promptly disabled , losing her rudder , her mainmast and her bowsprit . " Cornwall " also endured heavy gunfire , losing some of her stern . Both ships had to be towed to open sea , having lost about 100 men killed and more than 200 wounded . Next day , after discuss how the obstacle could be removed , Knowles led his squadron back to Jamaica . Aftermath . After having his ships refitted Knowles sailed on a cruise , hoping to intercept the Spanish treasure fleet off Cuba . On 30 September he fell in with HMS " Lenox " , under Captain Charles Holmes , who reported that he had encountered a Spanish fleet some days earlier . The fleet was sighted the next morning but confusion over signals and a struggle to keep the weather gauge meant that the British fleet failed to attack in an organised manner . Though the Battle of Havana ended with the capture of one Spanish ship and another being badly damaged , it was not the major British victory hoped for . Knowles was accused of badly mismanaging the action and faced a court martial in December 1749 . The result was a reprimand for the poor tactics he employed , while several of the other captains involved were also reprimanded . There was considerable bad feeling between Knowles and his subordinates , and several challenges to duel were issued . In once instance Knowles exchanged shots with Holmes , and in another two of his captains , Innes and Clarke , duelled , which resulted in Innes being mortally wounded . King George II eventually intervened to forbid any more duels over the matter .