| Date | | | |
| 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. | |
| 1517 | | The mayor and light-armed citizens marched out against O'Toole,but were forced to retreat with some loss. | |
| 1521 | | The armed citizens perform good services under the Earl of Surrey, against O'More in Leix, and O'Connor in Meath. | |
| 1525 | | A plague throughout Ireland, and more particularly in Dublin, caused by a very hot summer and wet autumn. Con O'Neal and Hugh Roe O'Donncl came to Dublin to settle their disputes with the lord deputy, the Earl of Kildare, and the Council, but returned without coming to an amicable agreement. | |
| 1531 | | A great riot in High-street between the soldiers and city apprentices. | |