| 1172 | Anglo-Norman invasion of Ireland during the reign of Henry II |
| 1485-1509 | reign of Henry VII |
| 1492 | the 8th earl of Kildare (head of the Fitzgerald family and the most important Irish lord) is deprived of his position for supporting Perkin Warbeck's rebellion against Henry VII |
| 1494 | Poynings' Law |
| 1496 | the earl of Kildare is reappointed Deputy of Ireland when governing Ireland directly proves too costly for the English crown |
| 1509-1547 | reign of Henry VIII |
| 1530s | Thomas Cromwell tries to bring Ireland under control through the policy of surrender and regrant; Cromwell dismisses the 9th earl of Kildare |
| 1534 | rebellion of Silken Thomas (son of the earl of Kildare) |
| 1535 | Silken Thomas surrenders |
| 1536 | the Act of Union begins the process of assimilating the Welsh; the Irish Reformation Parliament meets |
| 1541 | Irish parliament confirms Henry VIII as King of Ireland |
| 1547-1553 | reign of Edward VI |
| 1553-1558 | reign of Mary I |
| 1553 | plantation of Laois and Offaly counties (renamed Queen's County and King's County) |
| 1558-1603 | reign of Elizabeth I |
| 1565 | appointment of Sir Henry Sidney as lord deputy of Ireland: the English government determines to bring all of Ireland under English control |
| 1569-1573 | James Fitzmaurice Fitzgerald leads the first Desmond rebellion in Munster against Sir Peter Carew, the English adventurer who had laid claim to estates of the Fitzgeralds and the Butlers; Fitzgerald is defeated and flees to the continent |
| 1579-1583 | Fitzgerald's second unsuccessful rebellion; Munster is laid bare |
| 1586 | plantation of Munster |
| 1588 | defeat of the Spanish Armada |
| 1591 | foundation of Trinity College, Dublin |
| 1594 | rebellion of Hugh O'Neill, earl of Tyrone |
| 1596 | Edmund Spenser writes A View of the Present State of Ireland |
| 1598 | Battle of the Yellow Ford: O'Neill defeats Sir Henry Bagenal; a general uprising in Munster sweeps away the plantation |
| 1599 | the earl of Essex arrives in Ireland but O'Neill outmaneuvers him |
| 1600 | Lord Mountjoy replaces Essex |
| 1601 | Battle of Kinsale: O'Neill and his Spanish allies defeated by Mountjoy |
| 1603 | Treaty of Mellifont; James Stuart becomes James I of England |
| 1607 | the flight of the earls: O'Neill, Rory O'Donnell and more than ninety other Ulster chiefs sail into voluntary exile |
| 1609 | plantation of Ulster |