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February - John de Cobham, 3rd Baron Cobham, is licensed to begin the 5-year fortification of Cooling Castle on the south side of the Thames Estuary; it is the earliest English castle designed for the use of gunpowder weapons by its defenders.
Spring - The third and final of a series of poll taxes designed to help pay for the war against France. This tax is highly unpopular, with many people blaming Simon Sudbury, at this time both Lord Chancellor and Archbishop of Canterbury.
30 May - Peasants' Revolt breaks out when the attempts of an official (John Brampton) to collect unpaid poll taxes in Brentwood, Essex, ends in violent confrontation.
15 June - Peasants' Revolt: During further negotiations, Wat Tyler is murdered by the King's entourage. Noble forces subsequently overpower the rebel army, the rebel leaders are captured and executed and Richard revokes his concessions.
Late June to July - Peasant revolts spread to St Albans and East Anglia, but are quickly suppressed. Norfolk rebels are defeated at the Battle of North Walsham (25 or 26 June).
The Canterbury city walls are being repaired. The ancient Roman walls are in disrepair and there has been concern that the French might raid the city. Murage is used for raising the money.
King Richard II tries to rule the country without Parliament.
1386
8 March - Richard recognises John of Gaunt as King of Castile, by right of his second marriage to the Infanta Constanza of Castile in 1371, and grants him control of all royal lands in Ireland.
July - John of Gaunt leaves England to make good his claim to the Crown of Castile.
October - The Wonderful Parliament is held, and appoints a commission to oversee the court and government.
(approx.) - Salisbury cathedral clock is started. By the 21st century it will be the world's oldest working clock.
1387
24 March - Hundred Years' War: A Franco-Castilian fleet is defeated off Margate.
14 November - A group of powerful nobles known as Lords Appellant raise arms against the King, demanding the arrest of members of the royal court.
20 December - Battle of Radcot Bridge: Lords Appellant defeat Richard's army. The king is imprisoned until he agrees to replace all the councillors in his court.
3 February - The entire court of King Richard II is convicted of treason by the Merciless Parliament, under the influence of the Lords Appellant, and are all either executed or exiled. Richard II effectively becomes a puppet of the Lords Appellant.
5 August - Battle of Otterburn: a Scottish army, led by James Douglas, defeats an English army, capturing their leader, Harry Hotspur. Douglas is killed during the battle.
The completion of Wycliffe's Bible by John Purvey and the beginning of prosecution of Wycliffe's followers, the Lollards.
John of Gaunt makes peace with Castile and gives up his claim to the Castilian throne by allowing his daughter Katherine of Lancaster to marry Prince Henry, the eldest son of John I of Castile.
1389
3 May - King Richard retakes control of the government.
18 July - Truce of Leulinghem: England and France sign a truce, ending the second phase of the Hundred Years' War and bringing a 13-year peace.