Battle of the Espero Convoy The Battle of the Espero Convoy was the first Second World War surface engagement between Italian and Allied warships . It took place southwest of Crete on 28 June 1940 , after a force of seven cruiser s and 16 destroyer s , preparing to escort three Allied convoys to Alexandria , were informed of the presence of an Italian flotilla of three destroyers . The Italian warships were bound from Taranto to Tobruk , carrying an anti - tank army unit to north Africa . Background . On 10 June 1940 , Italy declared war on Britain and France . The Italian High Command ( " Comando Supremo " ) expected a British Army advance into Cyrenaica led by armoured forces , and decided that an anti - tank unit should be moved to Tobruk as soon as possible . The unit comprised ten anti - tank guns , of ammunition , and 162 soldiers . Prelude . The Italians chose three " Turbine " - class destroyer s to transport the anti - tank unit , for their high speed ( ) and loading capacity . The three chosen were " Espero " ( flagship ) , " Zeffiro " and " Ostro " . The Italian flotilla was commanded by " Capitano di Vascello " Enrico Baroni . At the same time , three Allied convoys — two from Malta and another from Greece — were to be brought to Alexandria , covered by seven cruisers ( two light cruiser s — and — and five of the 7th Cruiser Squadron : ( flagship ) , , , and ) and 16 destroyers . The British warships were commanded by Vice - Admiral John Tovey . The Allied operation was supported by Short Sunderland flying boat s from Alexandria and Malta . Battle . The Italian destroyers were found at noon by two Sunderlands some west of Zante island . They were within striking range of Tovey ’ s 7th Squadron , so he ordered them to intercept the Italians in two divisions . The first salvoes from the Allied cruisers were fired at 18 : 30 at the surprised Italian flotilla at a range of . Baroni realised that — despite the best speed of his ships — they were hopelessly outgunned . He therefore decided to sacrifice " Espero " in order to enable the other two to escape : " Espero " laid smokescreens and conducted evasive manoeuvres . " Zeffiro " and " Ostro " headed safely to the southwest at full speed . Despite heavy firing , " Espero " was not hit until 19 : 20 , when the range had closed to . By this time , Tovey had given up the chase of the other two destroyers . The 7th Squadron expended about 5 , 000 shells before " Espero " was sunk , after 130 minutes of fierce fighting . A single Italian shell hit HMS " Liverpool " , but caused little damage . The battle exacerbated a shortage of ammunition at Alexandria so that the planned Malta convoys were suspended for two weeks . HMAS " Sydney " rescued 47 men from the Italian destroyer , and six others were later found alive by an Italian submarine almost 20 days later . Captain Baroni died aboard his ship , and was posthumous ly awarded the " Medaglia d´oro al valor militare " . " Zeffiro " and " Ostro " both reached Benghazi the next day and arrived at Tobruk shortly after . Two - thirds of the convoy had been saved . Aftermath . There were lessons learned by both sides after this battle . For the Allies , the battle showed that a daylight naval action at long range was unlikely to be decisive when the enemy units outmatched one ' s own speed . For the Italians , this was a grim lesson about the importance of well - coordinated air surveillance . Had Italian aircraft spotted the Allied cruisers before they came within range , all three destroyers would have escaped unscathed .