Evacuations of Allied Forces from Crete Begins

Over four nights, 16,000 troops were evacuated to Egypt by ships including the light cruiser HMS Ajax.

The majority of these troops embarked from Sphakia. A smaller number were withdrawn from Heraklion on the night of 28 May. This task force was attacked en route by Luftwaffe dive-bombers and suffered serious losses. More than 9,000 Anzacs and thousands of Greeks were left behind to defend the remaining territory as best they could. They fought on until they were surrounded. The cities of Irakleio and Rethymno were taken in the following days by the Germans. A small Italian force assisted the capture of Rethymno. By 1 June, the island of Crete was under German control.

The defence of the 8th Greek Regiment in and around the village of Alikianos is credited with protecting the Allied line of retreat. Alikianos, located in the "Prison Valley", was strategically important and it was one of the first targets the Germans attacked on the opening day of the battle. The 8th Greek was composed of young Cretan recruits, gendarmes, and cadets. They were poorly equipped and only 850 strong – roughly battalion, not regiment-sized. Attached to the 10th New Zealand Infantry Brigade under Lieutenant-Colonel Howard Kippenberger, little was expected of them by Allied officers. The Greeks, however, proved such pessimism wrong. On the first day of battle, they decisively repulsed the Engineer Battalion. During the next several days, they held out against repeated attacks by the 85th and 100th Mountain Regiments. For seven days, they held Alikianos and protected the Allied line of retreat. The 8th Greek Regiment is credited with making the evacuation of western Crete possible by many historians such as Antony Beevor and Alan Clark.

The Germans pushed the British, Commonwealth, and Hellenic forces steadily southward, using aerial and artillery bombardment, followed by waves of motorcycle and mountain troops (the mountainous terrain making it difficult to employ tanks). The Souda Bay garrisons at Souda and Beritania gradually fell back along the lone road to Vitsilokoumos, just to the north of Sphakia. About halfway there, near the village of Askifou lay a large crater nicknamed "The Saucer". It was the only spot in the rugged terrain sufficiently wide and flat enough to support a large-scale air drop. Troops were stationed about its perimeter to prevent a German airborne force from landing to block the retreat. At the village of Stilos, the 5th New Zealand Brigade and the 2/7th Australian Battalion held off a German mountain battalion which had begun a flanking manœuvre, but they were forced to withdraw for lack of air and artillery support, despite their superior numbers. Fortunately for the ANZACs, German air assets were being concentrated on Rethymnion and Heraklion, and they were able to retreat down the road safely in broad daylight.

The general retreat of the brigade was covered by two companies of the 28th (Māori) Battalion under Captain Rangi Royal. (Royal's men had already distinguished themselves at 42nd Street.) They overran the 1st Battalion, 141st Gebirgsjäger Regiment and halted the German advance. When the main unit was safely to the rear, the Māori in turn made their own fighting retreat of twenty-four miles, losing only two killed and eight wounded, all of whom they were able to carry to safety. Thus, the Layforce commando detachment was the only major unit in this area to be cut-off and unable to retreat.

Layforce had been sent to Crete by way of Sphakia when it was still hoped that large-scale reinforcements could be brought in from Egypt to turn the tide of the battle. The battalion-sized force was split up, with a 200-man detachment under the unit's commander, Robert Laycock, stationed at Souda to cover the retreat of the heavier units. Laycock's men, augmented by three of the remaining British tanks, were joined by the men of the 20th Heavy Anti-Aircraft Battery, who had been assigned to guard the Souda docks and refused to believe that a general evacuation had been ordered. After a day's fierce fighting, Laycock decided to retreat under cover of night to nearby Beritiana. He was joined there by Captain Royal and the Māoris, who took up separate defensive positions and eventually made their fighting retreat. Laycock and his force, however, were cut off by superior German forces near the village of Babali Khani. Pummelled from the air by dive bombers, Layforce Detachment was unable to get away. Laycock and his brigade major, the novelist Evelyn Waugh, were able to escape by crashing through German lines in a tank. Most of the other men of the detachment and their comrades from the 20th were either killed or captured.

During the evacuation, Admiral Cunningham was determined that the "Navy must not let the Army down". When Army officers expressed concerns that he would lose too many ships, Cunningham said that "It takes three years to build a ship, it takes three centuries to build a tradition".

Major Alistair Hamilton, a company commander in the Black Watch, had declared, "The Black Watch leaves Crete when the snow leaves Mount Ida". Hamilton himself never left the island; he was killed by a mortar round, but his men were ordered off, and they reluctantly complied. The consensus among the men was that they were letting their Greek allies down, and while most British heavy equipment was destroyed in order to keep it from falling into enemy hands, the men turned over their ammunition to the Cretans who were staying behind to resist the Germans.

Immediately after landing on 28 May, the parachute units contacted the embattled pocket force and launched a concerted attack against the British positions, eliminating several enemy strongholds with the support of dive-bombers. After regrouping his forces during the night the German commander at Iraclion set out to capture the town and the airfield early on the next morning. At daybreak the German troops closed in on the British positions. Not a shots was fired. British naval vessels had evacuated the Iraclion garrison during the preceding night. By that time British resistance had crumbled everywhere. German supplies and equipment were landed at Souda Bay without interference from enemy naval or air units.