| year | event |
| 1327 | Edward II dies, Edward III becomes King of England |
| 1330 | Edward, Black Prince of Wales, heir to Edward III is born |
| 1338 | Lionel of Antwerp (Clarence), second heir to Edward III, is born |
| 1340 | John of Gaunt (Lancaster), third heir to Edward III, is born |
| 1341 | Edmund of Langley (York), fourth heir to Edward III, is born |
| 1355 | Phlippa of Ulster, daughter of Lionel of Antwerp, is born |
| 1359 | John of Gaunt marries Blanche of Lancaster |
| 1364 | Henry Percy (Hotspur) is born… three years before Bolingbroke is born |
| 1365 | Edward of Angouleme, son to Edward Black Prince of Wales, is born |
| 1367 | Richard of Bordeaux, son to Edward Black Prince of Wales (and future Richard II), is born |
| Henry Bolingbroke, son to John of Gaunt, and future Henry IV, is born |
| 1368 | Lionel of Antwerp (Clarence), second heir to Edward III, dies |
| Phlippa of Ulster, daughter of Lionel of Antwerp, marries Edmund Mortimer 3rd Earl of March |
| 1369 | Blanche of Lancaster, wife to John of Gaunt, dies |
| 1371 | Elizabeth Mortimer, daughter to Philippa of Ulster and Edmund Mortimer 3rd Earl of March, is born |
| 1372 | Edward of Angouleme, son to Edward Black Prince of Wales, dies |
| 1374 | Roger Mortimer 4th Earl of March, son to Philippa of Ulster and Edmund Mortimer 3rd Earl of March, is born |
| 1376 | Edward Black Prince of Wales, heir to Edward III, dies |
| Edmund Mortimer, son to Philippa of Ulster and Edmund Mortimer 3rd Earl of March, is born |
| 1377 | Edward III dies |
| Richard II crowned King of England at age ten |
| 1379 | Henry Hotspur Percy marries Elizabeth Mortimer, daughter of Philippa of Ulster and Edmund Mortimer 3rd Earl of March |
| 1381 | Edmund Mortimer 3rd Earl of March dies |
| 1382 | Richard II marries Anne of Bohemia |
| 1386 | Henry Bolingbroke marries Mary de Bohun, sister of Eleanor de Bohun, making Gloucester and Bolingbrook both uncle and nephew AND brothers-in-law |
| 1387 | Prince Hal, son of Henry Bolingbroke, and future Henry V, is born |
| 1388 | Hotspur defeats the Scots and 2nd Earl of Douglas |
| 1389 | John, son of Henry Bolingbroke, is born |
| 1394 | Anne of Bohemia dies of plague without providing an heir for Richard II |
| Constance of Castille, John of Gaunt's second wife, died |
| Mary de Bohun, wife of Henry Bolingbroke, dies |
| 1396 | John of Gaunt marries (again) Katherine Swinford, with whom he had fathered four children in the 1370's |
| 1397 | Thomas of Woodstock (Gloucester), fifth heir to Edward III, is murdered in prison (presumably under Richard II's order) |
| 1398 | EVENTS OF RICHARD THE SECOND BEGIN (both Bolingbroke and Richard are 31 years old, and Richard is in the 21st year of his reign) |
| 1400 | EVENTS OF RICHARD THE SECOND END (Richard dies in captivity [February 14]) |
| Owen Glendower begins his rebellion against the English |
| 1402 | Battle of Bryn Glas: Welsh leader Owen Glendower captures Edmund Mortimer (June) |
| Edmund Mortimer marries Catrin Glendower, daughter of Owen Glendower |
| Hotspur defeats the Scots and Mordake (the son of the regent of Scotland) (September) |
| EVENTS OF THE FIRST PART OF HENRY THE FOURTH BEGIN |
| 1403 | Battle of Shrewsbury (July) |
| EVENTS OF THE FIRST PART OF HENRY THE FOURTH END |
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