During the last days of preparation for Operation Mercury the German high command decided that it was too risky to rely only on the airborne assaults and hastily assembled a flottilla of confiscated caïques and fishing boats in the port of Piraeus.
The Regia Marina was asked to escort the convoy but given the sudden request and the losses on the Battle of Cape Matapan could not provide much help.
The German convoy departed the 19th May along with the torpedo boat Sirio who had to stop shortly after for a propeller malfunction while 7 boats of the convoy had to turn back due to various failures.
The torpedo boat Curtatone was supposed to substitute Sirio but it sank due to a mine in the gulf of Athens, the task of escorting was then assigned to the torpedo boat Lupo (Italian for wolf).
Italian torpedo boat Lupo
Amidst delays and confusion the Lupo reached the other vessels the 21th and proceeded towards Creete along them afterwards, Allied naval action was not expected given the Axis air superiority (on the same day HMS Juno was sunk by Italian planes near the island) and the warship’s main role was supposed to be mainly guidance.
Things took a turn for the worst when night came and the Lupo sighted the destroyer Janus, after launching two torpedoes at the enemy the Italian ship started laying a protective smoke screen for the convoy, in the meantime the horizon started filling with other dark shapes: a while force consisting in three cruisers and four destroyers commanded by rear admiral Irvine Glennie was approaching.
The Lupo bravely sped through the enemy formation firing with all its guns causing visible confusion and then managing to slip away, the Allied fleet suffered little damage, mostly by friendly fire while the Lupo was hit by no less than 18 shells but only 3 of those exploded.
The British found and destroyed most of the boat of the convoy afterwards thanks to radars but after their departure the Italian torpedo boat returned to the scene saving most of the Germans.
In conclusion the British were able to stop the landing attempt, only two small vessels reached Crete, but failed to sink the sole Italian escort who turned what could have been a massacre in a relatively small loss (about 300 dead).
The Lupo was nicknamed “the luckiest ship in the Italian navy” and its commander received the Gold Medal of Military Valour for this action.
a sketch of the engagement (author unknown)