By 1261 the weakening of the Normans had become manifest when Fineen Mac Carthy defeated a Norman army at the Battle of Callan, Co Kerry and killed John fitz Thomas, Lord of Desmond, his son Maurice fitz John and eight other Barons. In 1315, Edward Bruce of Scotland invaded Ireland, gaining support of many Gaelic Lords against the English. Although Bruce was eventually defeated at the Battle of Faughart, the war caused a great deal of destruction, especially around Dublin. In this chaotic situation, local Irish lords won back large amounts of land that their families had lost since the conquest and held them after the war was over.

The Black death arrived in Ireland in 1348. Because most of the English and Norman inhabitants of ireland lived in towns and villages, the plague hit them far harder than it did the native irish, who lived in more dispersed rural settlements. After it had passed, Gaelic Irish language and customs came to dominate the country again. The English controlled area shrunk back to the Pale, a fortified area around Dublin that ran through the counties of Louth, Meath, Kildare and Wicklow and the Earldoms of Kildare, Ormonde and Desmond. Outside the Pale the Hiberno-Norman lords adopted the Irish language and customs, becoming known as the Old English, and in the words of a contemporary English commentator, became " more Irish than the Irish themselves. "

Over the following centuriesthey sided with the indigenous Irish in political and military conflicts with England and generally stayed Catholic after the Reformation. The authorities in the Pale grew so worried about the " Gaelicisation " of Ireland that they passed special legislation in a parliament in Kilkenny ( known as the Statutes of Kilkenny ) banning those of English descent from speaking the Irish language, wearing Irish clothes or inter-marrying with the Irish. Since the government in Dublin had little real authority, however, the Statutes did not have much effect.

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