| Timeline |
| 1343~ |
Born in London to a prosperous wine merchant and deputy to the kings's butler, and his wife Agnes (date approximate) |
| 1357 |
Becomes page in the household of Elizabeth de Burgh, Countess of Ulster |
| 1359 |
Off to France with Edward III's army during the Hundred Years' War |
| 1360 |
Captured in the Ardennes and returned to England after the treaty of Brétigny, diplomatic errands for Prince Lionel |
| 1366 |
Marries Philippa Roet, travels to Spain |
| 1367 |
Enters service as an esquire in the household of Edward III, son Thomas is born |
| 1368 |
Book of the Duchess |
| 1368 |
Appointed a Member of Parliament for Kent |
| 1369 |
Travels to Northern France and serves in the army of John of Gaunt |
| 1370 |
Travels to the Continent (France probably) on the King's service, again serves with the army in France |
| 1372 |
Travels to Italy on a diplomatic mission |
| 1374 |
Works as a government official at the port of London, holding the post of Comptroller of the Customs and Subside of Wools, Skins, and Tanned Hides |
| 1376 |
Journeys to France and Flanders to negotiate for peace and the marriage of Richard with a French princess |
| 1378 |
Travels to Italy on a diplomatic mission |
| 1380 |
Accused, and acquitted of the 'raptus' of Cecily Champain, Cecily later signs a document releasing him of charges, son Lewis born |
| 1385 |
Serves as Justice of the Peace for Kent until 1389 |
| 1386 |
The Legend of Good Women |
| 1387 |
Philippa dies, begins The Canterbury Tales |
| 1388 |
The House of Fame |
| 1389 |
Appointed clerk of the Works at Westminster, Tower of London, and other royal estates |
| 1390 |
Appointed Commissioner of Walls and Ditches |
| 1391 |
retired from Clerkship of the King's works, appointed Deputy Forester of the Royal Forest of North Petherton, Somerset |
| 1392 |
The Treatise of the Astrolabe |
| 1400 |
The Complaint of Chaucer to His Purse, dies 25 October and is buried in Westminster Abbey |
