| Date | | | |
| 1399 | | Richard II. arrived in Dublin the second time with a large train, and was nobly entertained by the provost. | |
| 1402 | | The O'Beirnes defeated with great slaughter by the citizens of Dublin, commanded by John Drake, provost. A parliament held in Dublin. | |
| 1404 | | Another parliament opened in Dublin, wherein the statutes of Dublin and Kilkenny, and the Charter of Ireland, were confirmed. | |
| 1406 | | A parliament held in Dublin, and adjourned to Trim. The citizens defeat the Irish of Wicklow, and fix the heads of the slain over the city gates. | |
| 1407 | | The franchises perambulated by the mayor and citizens. Licence granted to the mayor to have a gilt sword borne before him, in like manner as the mayor of London, as a reward for the services performed by the city of Dublin to the crown. | |
| 1408 | | Thomas of Lancaster, the king's son, having landed at Carrickfergus as lord lieutenant, arrived in Dublin, and arrested the Earl of Kildare. A parliament held in Dublin. | |
| 1409 | | Thomas Cusack chosen first mayor of Dublin, and Richard Boye and Thomas Shortall, bailiffs. | |
| 1410 | | The lord deputy, with the aid of the citizens, invaded the territory of the O'Beirnes, but was forced to retreat. A parliament in Dublin, which continued three weeks. | |
| 1411 | | Birmingham Tower, Dublin Castle, built. | |
| 1412 | | Hugh, son of O'Neil, escaped from prison in Dublin with the hostages sent thither with him. | |