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| 1300 | Bailiffs of Guernsey and Jersey are given separate seals of office |
| 1307 | The market in Guernsey moves from Landes du Marche to Town. |
| 1327 | Edward III becomes King following the murder of his father and in response to a plea from Guernsey, the construction of a further castle, this time at Jerbourg |
| 1337 | The Guernsey Militia formed |
| 1338 | The Hundred Years War began and Guernsey Alderney and Sark were seized by the French in retaliation, led by Sir Robert Bertram, Lord of Bricquebec |
| 1340 | Edward III defeated the King of France at the Battle of Sluys and then set about liberating Guernsey through the command of Walter de Weston which he did in October except for Castle Cornet which held out for another five years. |
| 1356 | Once again the islands were invaded by the French early that year but the Treaty of Calais in September saw the French abandon all claims to the Channel Islands. |
| 1361 | First hospital to be built in Guernsey |
| 1373 | French invade Jersey (except for Gorey Castle) but this lasted only a few weeks. |
| 1392 | St Appoline chapel built by Nicholas Henry |
| 1412 | Henry V becomes King and shortly afterwards he ousts the monks of St Michel from Sark. However in those days Sark was very inhospitable with no decent harbour and drinking water was in short supply. |
| 1415 | Henry V defeats the French at Agincourt and once again has control of most of northern France except Mont Michel. |
| 1455 | The War of the Roses began and was not to end until 1486. However during this period, Margaret of Anjou the wife or Edward IV, gifts the entire Channel Islands to her cousin Pierre de Breze. Afraid that they would lose their independence under French rule, the Channel islanders fought back under the leadership of Philippe de Carteret. He seized Mont Orgueil Castle in Jersey with the English naval fleet assisting. Guernsey was liberated soon afterwards. Later Edward IV and King Louis XI of France reconfirmed the treaty of Calais and the Channel Islands were declared neutral territory. |
| 1468 | Further Royal Charter granted to the islands from Edward IV |
| 1470 | |
| 1481 | First recorded meeting of the States of Guernsey. |
| 1486 | First Governor of Guernsey, Edmund Weston, is appointed |
| 1546 | Henry VIII was determined to turn an Alderney into a naval base and fortifications were starting to be built. The fort Les Murs de Haut was started but was not completed until the Victorian era and was bought by the Earl of Essex from John Chamberlain in 1591. |
| 1547 | Henry VIII had already fallen out with Catholic principles following his divorce from Catherine of Aragon in 1533 and the Channel Islands showed their support to him by scrapping all evidence of a Catholic faith. A Calvinist faith emerged. |
| 1549 | French troops seized the uninhabited island of Sark and built several forts but lost interest and eventually left the island. |
| 1556 | Catherine Cauches and her two daughters were burnt at the stake in Guernsey on suspicion of heresy (it was said that they did not attend mass). They appear in Foxe's book of Martyrs. |
| 1560 | Royal Charter granted to the islands by Elizabeth I. |
| 1563 | First Principal appointed at Elizabeth College |
| 1565 | Helier de Carteret from Jersey offered to colonise Sark and Queen Elizabeth I granted the island to de Carteret in perpetuity. The Queen later granted him a Royal Fief and in return he was obliged to maintain on the island at least 40 men and on demand, a horseman wearing a coat of mail. |
| 1576 | Calvinist principles introduced to all parishes in Guernsey |
| 1583 | Privy Council approve a statement of Guernsey's laws |
| 1598 | Elizabeth I authorises Guernsey Privateers to attack the French. |