| 1327 | Edward II is deposed Edward III becomes King Isabella & Mortimer govern Scots invade England |
| 1328 | Edward III recognizes Robert the Bruce as King of Scotland |
| 1329 | Edward II died, almost certainly murdered David II, King of Scots |
| 1330 | Mortimer arrested and executed Edward III seizes power and executes Mortimer |
| 1332 | Edward Balliol invades Scotland and is crowned King |
| 1333 | Scots expel Edward Balliol Edward III defeats the Scots at Halidon Hill |
| 1334 | David II of Scots flees to France |
| 1337 | Start of 100 Years War |
| 1340 | England win naval victory over French |
| 1341 | David II returns to Scotland |
| 1346 | England defeats France at Crecy Edward defeats a Scottish invasion and captures David II |
| 1348 | Order of the Garter is founded The Black Death reaches England |
| 1355 | The Hundred Years' War is renewed |
| 1356 | Edward the Black Prince defeats the French at Poitiers John II of Scotland is captured |
| 1357 | Edward III releases David II |
| 1361 | Edward, the Black Prince fights in Spain and contracts a disease |
| 1376 | Edward, the Black Prince dies |
| 1377 | Edward III dies Richard II becomes King of England John Of Gaunt is Steward of England |
| 1381 | Peasants' Revolt |
| 1387 | Lord Appellants win victory |
| 1388 | Merciless Parliament |
| 1390 | Robert III, King of Scots |
| 1394 | Richard II leads successful invasion of Ireland |
| 1398 | Henry Bolingbroke exiled |
| 1399 | Death of John of Gaunt Richard II deposed Henry IV becomes King of England Richard II confiscates Bolingbroke's inheritance Henry of Lancaster (Bolingbroke) deposes Richard II |
| 1400 | Richard II dies |
| 1402 | Sir Henry Percy wins victory over Scots |
| 1403 | Percys Revolt Henry IV victorious at Shrewsbury Sir Henry Percy killed |
| 1405 | Henry IV crushes Scrope's rebellion |
| 1406 | James I, King of Scotland |
| 1408 | End of Percys Revolt |
| 1413 | Henry V becomes King of England |
| 1415 | Henry V is victorious at Agincourt |
| 1420 | Treaty of Troyes declares Henry V heir to the French throne |
| 1422 | Henry VI becomes King Humphrey of Gloucester and John of Lancaster - protectors |
| 1429 | Joan of Arc is victorious at Orleons Charles VII of France crowned at Rouen |
| 1431 | Joan of Arc burned at Rouen |
| 1437 | James II, King of Scots |
| 1445 | Henry VI marries Margaret of Anjou |
| 1453 | The Hundred Years' War ends at Castillon |
| 1454 | Henry VI temporarily insane - Richard of York protector |
| 1455 | Wars of the Roses begin St Albans - Yorkists defeat Lancastrians. Beaufort dies. |
| 1460 | Warwick captures Henry VI at Northampton James III, King of Scots |
| 1461 | Edward IV wins at Towton and is crowned King Magaret and Henry flee to Scotland |
| 1465 | Henry VI is recaptured and imprisoned in the Tower |
| 1469 | Earl of Warwick and Duke of Clarence plot against Edward IV. Henry VI is restored to the throne and Edward flees to Flanders |
| 1471 | Edward IV lands in England, defeats Warwick at Barnet Imprisons Henry VI who is later murdered |
| 1483 | Edward IV dies Edward V, King of England Richard of Gloucester imprisons Edward V and his brother in the Tower where they disappear Richard III declared King of England |
| 1485 | Henry Tudor defeats and kills Richard III at Bosworth Crowned Henry VII, King of England |
| 1486 | Henry VII marries Elizabeth of York |
| 1487 | Lambert Simnel's rebellion crushed |
| 1488 | James IV, King of Scots |
| 1491 | Perkin Warbeck claims the throne |
| 1497 | Warbeck captured by Henry VII |
| 1501 | Prince Arthur and Catherine of Aragon marry in London |
| 1502 | Prince Arthur dies |
| 1503 | Betrothal of Prince Henry to Catherine of Aragon James IV of Scots marries Margaret Tudor, Henry's daughter |
| 1509 | Henry VII dies Henry VIII becomes King Henry VIII marries Catherine of Aragon |
| 1513 | Henry VIII defeats France at the Battle of Spurs James IV of Scots invades England and is defeated and killed at Flodden James V, King of Scots |
| 1514 | Wolsey becomes Archbishop of York Mary Tudor, Henry's sister, marries Louis XII of France |
| 1515 | Wolsey becomes Lord Chancellor and cardinal Francis I becomes King of France |
| 1516 | Birth of Princess Mary |
| 1518 | Wolsey made Papal Legate |
| 1519 | Charles V becomes Holy Roman Emperor |
| 1520 | Henry VIII meets Francis I of France at the Field of the Cloth of Gold. |
| 1529 | Wolsey falls from power Sir Thomas More becomes Chancellor |
| 1531 | Thomas Cromwell becomes a privy councillor |
| 1533 | Henry VIII secretly marries Anne Boleyn Cranmer is made Archbishop of Canterbury Cranmer grants Henry's divorce Birth of Princess Elizabeth |
| 1534 | Act of Supremacy |
| 1536 | Catherine of Aragon dies Anne Boleyn is executed Henry VIII marries Jane Seymour |
| 1537 | Prince Edward is born Jane Seymour dies |
| 1538 | James V of Scots marries Mary of Guise Henry VIII is excommunicated |
| 1540 | Henry VIII marries and divorces Anne of Cleves Thomas Cromwell is executed Henry VIII marries Catherine Howard |
| 1542 | Catherine Howard executed English defeat Scots at Solway Moss Mary Queen of Scots becomes queen |
| 1543 | Henry VIII marries Catherine Parr |
| 1547 | Henry VIII dies Edward VI becomes King of England and Ireland Edward Seymour, Duke of Somerset, becomes lord Protector |