Historically, during the 1590s, a Macleod chief lent support to certain Irish forces rebelling against those supporting Elizabeth I in Ireland. In the summer of 1594, Dòmhnall Gorm Mòr MacDhòmhnaill (chief of the Macdonalds of Sleat) and Ruairidh Mòr MacLeòid (chief of the Macleods of Harris and Dunvegan) both sailed for Ulster at the head of 500 men each. Their force was intended to support Aodh Ruadh Ó Domhnaill who was besieging Enniskillen Castle. After landing at Loch Foyle, the Hebridean chieftains were entertained by Ó Domhnaill for three days and three nights. MacDhòmhnaill then returned to the Hebrides and left his men behind in Ireland, however, MacLeòid stayed and was present at the fall of Enniskillen Castle in October 1594. He was still in Ireland the next year at the head of 600 Hebrideans, alongside Ó Domhnaill at the siege of MacCostello's Castle, in County Mayo. In light of Ruairidh Mòr's participation in activities in Ireland at the end of the 16th century, R.C. MacLeod concluded that the cup passed into the hands of the Macleods through the O'Neill chieftain Shane Ó Neill; and that the two chieftains were the friends mentioned in the traditional tale related by Lady O'Neill in 1925.