Battle of Glendale ( Skye ) The Battle of Glendale was a battle fought on the Inner Hebridean island of Skye , between the MacDonalds of Sleat and the MacDonalds of Clanranald , against the MacLeods of Harris and Dunvegan and the MacLeods of Lewis . According to MacLeod tradition preserved in the early 19th century , the battle was fought in about the year 1490 ; yet it has been recently suggested that the battle more likely took place sometime after 1513 . MacLeod tradition records that the battle was the ' most tremendous battle ' that the clan ever fought — although the clan was victorious , it never fully recovered from its severe losses . MacLeod tradition relates how the MacDonalds originally had the upper hand during the conflict , but when the MacLeod ' s sacred Fairy Flag was unfurled the MacLeods gained heart and won the battle . Conflict . According to MacLeod tradition preserved in the " Bannatyne manuscript " , a force of MacDonalds led by Donald Gruamach MacDonald , landed on Skye at Loch Eynort , in about the year 1490 . The MacDonalds proceeded to lay waste to the lands of Minginish , Bracadale , and Duirinish ; and their forces got right up to the gates of Dunvegan Castle . The manuscript states that during this time , the chief of the MacLeods of Harris and Dunvegan , Alasdair Crotach , was on the Outer Hebridean island of Harris ; but that upon hearing the news of the MacDonald ' s encroachments , he proceeded with all haste to Skye . The manuscript states that he landed at Glendale , where he was joined by his kinsmen , the MacLeods of Lewis . The historian J . L . Roberts noted that they would have landed at the head of Loch Poolteil , where the Glendale valley reaches the sea . The manuscript continues , that the combined MacLeod forces drew up on the brow of a hill , with a river in front of them which made it difficult for the MacDonalds to attack . The Bannatyne manuscript relates how the combined MacLeod forces waited ten days for reinforcements , until Donald Mor of Meidle arrived with a large force under his command . The battle then commenced ; the MacDonalds , however , gained the upper hand as Donald Mor was killed and hundreds of the MacLeods were killed . The MacLeods were just at the point of giving way when the mother of Alasdair Crotach ordered the Fairy Flag to be unfurled . With the magical flag unfurled , the manuscript states that the battle was renewed with redoubled fury , with immense losses on both sides . At one point , a party of MacDonalds , led by Allan MacDonald of Moidart ( chief of the MacDonalds of Clanranald ) , managed to cut off the MacLeod chief and the guardians of the Fairy Flag from the rest of their clan . However , just at that moment , Murdo MacCaskill slew Donald Gruamach MacDonald , raised his head upon a spear and ordered the MacLeod pipers to play the " MacDonald lament " . Disheartened by the ill - omened music and the loss of their leader , the MacDonalds broke and fled , disregarding attempts by the Clanranald chief to rally them . Roberts noted , that while the manuscript states that Donald Gruamach was killed at the battle , he was certainly alive in 1530 , and likely died several years later in 1534 . Roberts stated that if the battle actually occurred in the year 1490 , as the manuscript suggests , then it was many years before Donald Gruamach became chief of the MacDonalds of Sleat . Roberts considered it likely that several battles were confused in MacLeod tradition , and that the battle fought at Glendale was fought at a much later date than which MacLeod tradition records . Roberts proposed that MacDonalds could have landed on the north - west coast of Skye , following Alasdair Crotach ' s seizure of Dunscaith Castle after the year 1513 ; and that the opposing forces could have met and done battle at Glendale . Roberts noted that Alasdair Crotach later received a lease to the lands of Trotternish , from the Crown . These lands had been held at various times by Torquil MacLeod of Lewis , and Ranald Ban MacDonald of Clanranald . Roberts stated that in 1528 , Donald Gruamach joined forces with his half - brother , John MacLeod , eldest son of Torquil MacLeod of Lewis ; together the half - brothers drove Alasdair Crotach MacLeod out of Trotternish . Aftermath . According to the " Bannatyne manuscript " , the battle was said by the old clan shenachie s , that without descending from their perch , the raven s which stood on " Creggan nan Fitheach " ( " the Rocks of the Ravens " ) , drank the blood , and ate the flesh , of the MacDonalds who lay in heaps around . Allan of Moidart was to have fought in single combat with the Murdo MacCaskill , and three of his brothers , and slew them all , before retreating with the rest of the MacDonalds to their galleys at Loch Enyort . The manuscript states that the Battle of Glendale was " the most tremendous battle in which the MacLeods were ever engaged " . The victory was theirs , but it was bought at a terrible price : the clan ' s chief , Alasdair Crotach , was severely wounded , many of the leading men of the clan were dead , as well as most of the men of the clan . The manuscript states that the clan never fully recovered from these losses . Among the dead was Paul Dubh , the standard bearer , who carried the Fairy Flag in the battle until he was killed .