| Date | | | |
| 1488 | | Sir Richard Edgecombe arrives in Dublin to take the homage and oaths of fealty of the great men of Ireland. | |
| 1489 | | Muskets brought from Germany, and six of them presented to Gerald, earl of Kildare, lord deputy, who put them into the hands of the sentinels that mounted guard at his house in Thomas St. Another great plague. | |
| 1490 | | The first importation of claret into Dublin. | |
| 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. | |