| 1302 | Treaty of Caltabelotta ends the War of the Sicilian Vespers |
| 1307 | Edward II becomes king of England Trial of the Templars in France |
| 1308 | Henry of Luxembourg becomes Holy Roman Emperor |
| 1312 | Pope suppresses the Order of the Temple |
| 1313 | Lewis of Bavaria becomes Lewis IV, Holy Roman Emperor |
| 1314 | Battle of Bannockburn Louis X becomes king of France |
| 1316 | Philip V becomes king of France |
| 1322 | Charles IV becomes king of France |
| 1328 | Philip VI becomes king of France |
| 1330 | Edward III becomes king of England |
| 1337 | Hundred Years War begins |
| 1343 | Amadeus VI becomes count of Savoy (known as the Green Count) |
| 1346 | Battle of Crecy |
| 1354 | Edward III of England defaults on his loans; bankruptcy of the Bardi and Peruzzi |
| 1356 | Battle of Poitiers The Golden Bull is issued for the Holy Roman Empire |
| 1357 | The Jacquerie – peasant rebellions across France |
| 1358 | Jean I becomes king of France |
| 1360 | Trety of Brétigny |
| 1364 | Charles V becomes king of France |
| 1377 | Richard II becomes king of England |
| 1378 | The Ciompi Revolt in Florence |
| 1378-1381 | War of Chioggia between Venice and Genoa |
| 1380 | Charles VI becomes king of France |
| 1381 | Peasant Revolt in England |
| 1395 | Gian Galeazzo Visconti becomes the first duke of Milan |
| 1399 | Henry IV becomes king of England |
| 1402 | Death of Gian Galeazzo Visconti |
| 1405 | Venice conquers Verona, marking her expansion onto the mainland of Italy |
| 1407 | Assassination of Louis, Duke of Orleans |
| 1413 | Henry V becomes king of England |
| 1414 | Queen Giovanna of Naples begins her rule |
| 1415 | Battle of Agincourt |
| 1419 | Assassination of John the Fearless, Duke of Burgundy |
| 1420 | Treaty of Paris |
| 1422 | Henry VI becomes king of England Charles VII succeeds Charles VI in France |
| 1429 | Charles VII crowned king of France |
| 1434 | Cosimo de' Medici returns from exile; beginning of Medici rule in Florence |
| 1442 | Alfonso II becomes king of Naples |
| 1450 | Cade's Rebellion in England Francesco Sforza becomes duke of Milan, ending the Republic of St Ambrose |
| 1451 | Amadeus VIII becomes count of Savoy |
| 1454 | Peace of Lodi |
| 1455 | First Battle of St Albans; Wars of the Roses begins |
| 1458 | Genoa invites French rule of the city |
| 1459 | Ferrante I becomes king of Naples |
| 1461 | Louis XI becomes king of France |
| 1464 | Rebellion in France: le bien publique |
| 1471 | King Henry VI dies; Edward IV becomes undisputed king of England |
| 1477 | Charles the Bold dies in the Battle of Nancy |
| 1480 | Ludovico Sforza becomes duke of Milan |
| 1483 | Richard III becomes king of England Charles VIII becomes king of France |
| 1485 | Richard III killed at Battle of Bosworth Field; Henry Tudor becomes king Henry VII of England |
| 1494 | Charles VIII of France invades Italy |
| 1498 | Death of Savonarola in Florence |
| 1499 | Louis XII of France invades Italy |
| 1501 | Louis XII of France invades Italy a second time |
| 1508 | League of Cambrai formed |
| 1515 | Battle of Marignano |
| 1525 | Battle of Pavia |
| 1527 | Sack of Rome |