| rdfs:comment | - In April 1599, the Earl of Essex landed in Ireland with over 17,000 troops and cavalry to put down the rebellion of Hugh O'Neill and Red Hugh O'Donnell, which had spread from Ulster to all Ireland. To this end, he supported an Irish enemy of O'Donnell's, Sir Donogh O'Connor (O'Connor Sligo), encouraging him to repossess those territories of his in Sligo that O'Donnell had occupied.
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| abstract | - In April 1599, the Earl of Essex landed in Ireland with over 17,000 troops and cavalry to put down the rebellion of Hugh O'Neill and Red Hugh O'Donnell, which had spread from Ulster to all Ireland. To this end, he supported an Irish enemy of O'Donnell's, Sir Donogh O'Connor (O'Connor Sligo), encouraging him to repossess those territories of his in Sligo that O'Donnell had occupied. Sligo was an excellent advance base, with Ballyshannon 20 miles to the north-east commanding an important river-ford at the principal western passage into O'Donnell's country in Ulster. English military advisers had long urged the government councils in Dublin and London to capture these strategic points. O'Connor's brother-in-law, Tibbot na Long Burke (son of Gráinne O'Malley), was appointed joint-commander with an English captain of a force sailing from Galway, and O'Connor was expected to receive them in Sligo. However, O'Donnell quickly besieged O'Connor at Collooney Castle with over 2000 men in an effort to starve him out, and Essex was put on the back foot. Essex had no option but to support the besieged O'Connor, one of the few Gaelic chieftains the crown could rely upon for support. He ordered the experienced Sir Conyers Clifford, who was based in Athlone, to relieve the castle with 1,500 English infantry and 200 cavalry. It was hoped that the operation would also distract the chief rebel, O'Neill, and afford the crown an opportunity to march into his Ulster territory across its south-eastern border. O'Donnell left 300 men at Collooney Castle under his cousin, Niall Garbh O'Donnell, and sent another 600 to Sligo town to prevent the landing of English reinforcements under Tibbot na Long. He then marched to Dunavaragh with 1,500 of his men, where he was joined by additional forces under local chieftains Conor MacDermott and Brian Oge O'Rourke (son of Brian O'Rourke). The Irish then carefully prepared an ambush site in the Curlew Mountains, along the English line of march. O'Donnell had trees felled and placed along the road to impede their progress. When he got word of the English passing through Boyle, O'Donnell positioned his men. Musketeers, archers and javelin men were placed in the woods alongside the road to harass the English. The main body of Irish infantry, armed with pikes and axes, were placed out of sight behind the ridge of the mountain.
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