| Date | | | |
| 1492 | | The Earl of Ormond, with a large body of Irish, encamped at Thomas-court wood. | |
| 1493 | | John Sargent, mayor, imprisoned in the Castle, in consequence of a riot at Oxmantown, in which some of the citizens were killed. | |
| 1494 | | The fraternity of Arms of St. George abolished by parliament. | |
| 1497 | | A great dearth through many parts of Ireland. | |
| 1500 | | Dublin besieged by the Earl of Kildare. | |
| 1504 | | The mayor and armed citizens took part in the battle of Knocktuogh in Galway. Allen's hospital in Kevin-street founded. | |
| 1509 | | Henry VIII. proclaimed king in Dublin. | |
| 1512 | | The mayor of Dublin sentenced to do penance by walking barefooted through the city in public procession, in consequence of a riot in St. Patrick's Church, between the followers of the Earl of Ormond and the citizens who guarded the Earl of Kildare, lord deputy | |
| 1513 | | The mayor and armed citizens attended the Earl of Kildare in a hosting against O'Carrol; but the earl dying, the citizens returned home without having performed any action. | |
| 1516 | | The Earl of Kildare, son to the last-named earl, assisted by the citizens, routed the O'Tooles, slew their chieftain, and sent his head as a present to the mayor. | |