Anglo and Gaelic Ireland 1367–1536

Following Edward Bruces' failed attempt to reestablish centralized power throughout Ireland, the colony gave rise to a number of important Irish kingdoms and lordships by the late 14th and early 15th centuries. They were:

*Connacht. The O Conchobhair dynasty, despite their setback during the Bruce wars, had regrouped and ensured that the title King of Connacht was not yet an empty one. Their stronghold was in their homeland of Sil Muirdeag, from where they dominated much of northern and northeastern Connacht. However, after the death of Ruaidri mac Tairdelbach Ua Conchobair in 1384, the dynasty split into two factions, O Conchobhair Donn and O Conchobhair Ruadh. By the late 1400s, internecine warfare between the two branches had weakened them to the point where they themselves became vassals of more powerful lords such as O Domhnaill of Tir Connail and the Clan Burke of Clanricarde.

: The MacDermot Kings of Moylurg retained their status and kingdom during this era, and were frequently powerful kingmakers, right up to the death of Tadhg MacDermot in 1585 (last "de facto" King of Moylurg). Their cousins, the Mac Donnacha of Tir Ailella, found their fortunes bound to the O Conchobhair Ruadh. The kingdom of Hy-Many had lost much of its southern and western lands to the Clanricarde's, but managed to flourish until repeated raids by O Domhnaill in the early 1500s weakened it to mere lordship status. Other lordships such as O Flaithbeheraigh of Iar Connacht, O Shaughnessey of Aidhne, O Dubhda of Tireagh, O Hara, O Gara and O Maddan, either survived in isolation or were vassals for greater men.

*Ulster: The Ulaidh proper were in a sorry state all during this era, being squeezed between the emergent O Neill of Tir Eoghain on the west, the MacDonnells, Clann Aodha Buidhe, and the Anglo-Normans from the east. Only Mag Aonghusa managed to retain a portion of their former kingdom with expansion into Iveagh.

:The two great success stories of this era were O Domhnaill of Tir Connaill and O Neill of Tir Eoghain. O Domhnaill was able to dominate much of northern Connacht to the detriment of its native lords, both Old English and Gaelic, though it took time to subborn the likes of O Conchobhair Sligigh and O Ruairc of Iar Brefine. Expansion southwards brought the hegemony of Tir Eoghan, and by extension O Neill influence, well into the border lordships of Louth and Meath. Mag Uidir of Fer Managh would slightly later be able to build his lordship up to that of third most powerful in the province, at the expense of the O Ruaircs of East Brefine and the MacMahons of Oriel.

*Leinster: Likewise, despite the adverse effects (and unforeseen) effects of Diarmait Mac Murchada's efforts to regain his kingdom, the fact of the matter was that of his twenty successors up to 1632, most of them had regained much of the ground they had lost to the Normans, and exacted yearly tribute from the towns. His most dynamic successor was the celebrated Art mac Art MacMurrough-Kavanagh. The O Brioin and O Tuathail largely contented themselves with raids on Dublin (which, incredibly, continued into the 18th century). The O Mordha of Laois and O Conchobhar Falaighe of Offaly - the latter's capital was Daingean - were two self-contained territories that had earned the right to be called kingdoms due to their near-invincibility against successive generations of Anglo-Irish. The great losers were the O Melaghlins of Meath: their kingdom had collapsed, and despite the near-superhuman martial prowess of Cormac mac Art O Melaghlain, the royal family were now reduced to vassal status, clinging to the east shores of the River Shannon. Meath itself ceased to be a separate province and was henceforth incorporated into Leinster, reducing Ireland's provinces to four.

*Munster: Despite huge setbacks, the descendants of Brian Boru had, by surviving the Second Battle of Athenry and winning the decisive battles of Corcomroe and Dysert O'Dea, been able to subborn their vassals and eradicate the Normans from their home kingdom of Thomond. Their spheres of interest often met with conflict with Anglo-Normans such as the earls of Desmond and Ormonde, yet they ruled right up to the end of Gaelic Ireland, and beyond, by expedient of becoming the O Brien Earls of Thomond. The three MacCarthys — Mac Carthaigh Mor, Mac Carthaigh Riabhach and Mac Carthaigh Muscraighe — were, in the case of the latter two, often mere satellites of others, while the Mac Carthaigh Mor managed to take advantage of Munster's unusually self-contained character and preserve the kingdom.

To continue the events beyond the 1530s see: Tudor re-conquest of Ireland