1289. De Birmingham is defeated by the Irish of Offaly, under their king, Calbhach O'Conor.
1290. Toirdhealbach O'Domhnaill, "with the help of his mother's kindred, the MacDonnells of Scotland, and many other galloglasses," deposes his brother and makes himself king of Tir Conaill. This is the first mention of galloglasses by name and also of the MacDonnells as galloglass chiefs, in the Annals of Ulster, but the context indicates that the word was already in established use.
1291. The Red Earl exacts the hostages of Connacht and harries Tir Conaill.
1292. FitzGerald of Offaly rebuilds the castle of Sligo and takes the king of Connacht prisoner. Next year, this king, having got free, destroys the castle of Sligo.
1295. Geoffrey O'Farrell destroys three border castles of Meath. The O'Farrell territory was at this time a small part of the present county of Leitrim. It was gradually extended after this until it comprised the county of Longford in addition. Longford takes its name from Longphort Ui Fhearghail, "O'Farrell's camp," a name significant of the new military organisation.
1305. Sir Piers de Bermingham caused three of the Irish ruling family of Offaly and twenty-nine nobles of their people to be murdered at a banquet to which he had invited them in his own castle. For this he received a reward in money from the Viceroy and Council, with the consent of Ricard de Burgh, Earl of Ulster.
In the same year, the Earl of Ulster built a castle in Inishowen, no doubt with a view to commanding Loch Foyle and hindering the landing of galloglasses. It may be noted that the Irish name of Milford Haven, a little farther west, is Port na nGalloglach, "the port of the galloglasses." This year we find a MacSuibhne in command of galloglasses in Breifne.
1307. Donnchadh O'Ceallaigh, king of Ui Maine, in retaliation for the burning of his town of Ath Eascrach, attacks Roscommon, kills a great part of the defenders, and captures the Sheriff.
1308. The Foreigners of North Connacht are defeated by the Irish at Ballysodare.
1310. Geoffrey O'Farrell marches against Donore Castle in Westmeath, and Ruaidhri, king of Connacht, attacks the De Burgh castle of Bun Finne.