Hugh Roe O'Donnell was an important ally of Hugh O'Neill in the rebellions against Elizabeth I in the 1590s. He had actually been imprisoned in anticipation of his causing problems for the English authorities but was helped to escape by Hugh O'Neill.
Upon his return to Ulster, he gained the leadership of the O'Donnell Clan becoming Lord of Tyrconnell after his father abdicated in his favour. He successfully led two expeditions against Turlough Luineach O'Neill in 1593, in order to force Turlough O'Neill to abdicate his chieftainship in favour of Hugh O'Neill. At this point, O'Neill did not join O'Donnell in open rebellion, but secretly backed him in order to enhance his bargaining power with the English. O'Neill was also communicating with Philip II of Spain for military aid.
Declaring open rebellion against the English the following year, O'Donnell's forces captured Connacht from Sligo to Leitrim by 1595. Hugh O'Neill, Earl of Tyrone, abandoned negotiations with the English and combined forces with O'Donnell to defeat an English army under Sir Henry Bagenal at the Battle of Clontibret.
Their greatest victory came two years later at the Battle of the Yellow Ford on the Blackwater River near the southern border of Tyrone in August 1598. The Irish annihilated an English force marching to relieve Armagh and they seemed on the verge of expelling the English from Ireland altogether.
O'Neill then went south to secure the allegiance of Irish lords in Munster, without much success. O'Donnell raided Connacht, destroying the town of Athenry, laying waste to much of County Galway, and on being refused entry to Galway, burned its suburbs. As a result of these and other assaults, O'Donnell was unable to persuade the local lords to join him.
During the next two years, O'Donnell and O'Neill were hard pressed as thousands of English troops were poured into the country. O'Donnell repulsed an English expedition towards western Ulster at the battle of Curlew Pass in 1599, but his and O'Neill's position was increasingly defensive. Even worse for O'Donnell than English offensives was the defection of his kinsman, Niall Garve O'Donnell, to the English side, in return for their backing his own claim the O'Donnell chieftainship. Niall Garve's support allowed the English to land a seaborne force at Derry in the heart of O'Donnell's territory.
O'Neill and O'Donnell recognised that their only chance of winning the war outright was with the aid of a Spanish invasion. The Spanish finally landed at Kinsale - at virtually the opposite end of Ireland from the Ulster rebels in September 1601. O'Donnell was forced to lead his army in a hard march during the winter of 1601, often covering over 40 miles a day, to join O'Neill and the Spanish General Juan del Aguila at Kinsale. They arrived in early December 1601.
During the Battle of Kinsale on 5/6 January 1602 the combined forces of Del Aquila, O'Neill and O'Donnell were defeated by Sir Charles Blount, Lord Mountjoy.
O'Donnell fled to Spain to try and resurrect forces and support. It was widely rumoured at the time that Red Hugh had been poisoned by a hired assassin in 1602 by an English spy.
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