The 1390s was a decade of the Julian Calendar which began on January 1, 1390, and ended on December 31, 1399.
- January 19 – The Treaty of Lyck confirms an alliance between Vytautas and the Teutonic Knights, in the Lithuanian Civil War against Vytautas's cousin, Jogaila.
- April 14 – John VII Palaiologos overthrows his grandfather, John V Palaiologos, as Byzantine Emperor.
- April 19 – Robert III succeeds his father, Robert II, as King of Scotland.
- May 26 – The Treaty of Königsberg is signed in Königsberg, during the Lithuanian Civil War, between Samogitian nobles and representatives of the Teutonic Knights.
- September 11 – Lithuanian Civil War: The coalition of Vytautas and the Teutonic Knights begins a 5-week siege of Vilnius. The Duke of Hereford (the future King Henry IV of England) is among the western European knights serving with the coalition.
- September 17 – John VII Palaiologos seeks refuge with the Ottoman sultan Bayezid I, after John V Palaiologos is restored by his son, Manuel, and the Republic of Venice.
- October 9 – Henry III succeeds his father, John I, as King of Castile and León.
- The Ottomans take Philadelphia, the last Byzantine enclave of any significance in Anatolia.
- Barquq is restored as Mamluk Sultan of Egypt, after overthrowing Sultan Hadji II.
- Nasir ud din Muhammad Shah III overthrows his brother, Abu Bakr Shah, as Sultan of Delhi.
- Manuel III succeeds his father, Alexios III, as Emperor of Trebizond (now north eastern Turkey).
- Sikandar But-shikan succeeds Sikandar Shah, as Sultan of Kashmir.
- Ko Cheng succeeds Che Bong Nga, as King of Champa (now eastern Vietnam).
- Mahmud succeeds Sandaki as Mansa of the Mali Empire, restoring the Keita Dynasty.
- N'Diklam Sare succeeds Sare N'Dyaye, as ruler of the Jolof Empire (now part of Senegal).
- The Kingdom of Kaffa is established in present day Ethiopia (approximate date).
- Templo Mayor, the main temple of the Aztec capital of Tenochtitlan (now Mexico City), is built.
- The Candi Surawana Temple is built in the Majapahit Kingdom (now Indonesia).
- Construction begins on San Petronio Basilica in Bologna.
- Manuel II Palaiologos becomes Byzantine emperor after his father, John V Palaiologos, dies of a nervous breakdown, due to his continued humiliation by the Ottoman Empire.
- Yusuf II succeeds Muhammed V, as Nasrid Sultan of Granada (now southern Spain).
- Stephen Dabiša succeeds Stephen Tvrtko I, as King of Bosnia.
- Shah Mansur becomes leader of the Timurid-occupied Muzaffarid Empire, in central Persia.
- A group of Muzaffarids under Zafar Khan Muzaffar establish a new Sultanate at Gujarat, in western India.
- Vytautas the Great, claimant to the throne of Lithuania, forms an alliance with Muscovy.
- Roman I succeeds Petru, as Prince of Moldavia (now Moldova and north-eastern Romania).
- Konrad von Wallenrode succeeds Konrad Zöllner von Rotenstein, as Grand Master of the Teutonic Knights.
- Bridget of Sweden is canonized by Pope Boniface IX.
- Ushkuinik pirates from Novgorod sack the Muscovy towns of Zhukotin and Kazan.
- The Chinese invent toilet paper for use by their emperors.
- Henry I Sinclair, Earl of Orkney, takes control of the Shetland Islands and the Faroe Islands.
- The University of Ferrara is founded on the Italian Peninsula.
- The Ming government orders 50 million trees planted in the Nanjing area.
- King Jogaila of Poland and Lithuania appoints his cousin Vytautas the Great as regent of Lithuania, in return for Vytautas giving up his claim to the Lithuanian throne. Vytautas replaces Jogaila's unpopular brother Skirgaila as regent.
- Muhammed VII succeeds Yusuf II, as Nasrid Sultan of Granada (modern-day southern Spain).
- Franciscan friar James of Jülich is boiled alive, for impersonating a bishop and ordaining his own priests.
- Maria, Queen of Sicily defeats an army of rebel barons.
- William le Scrope succeeds William II de Montacute, as King of Mann.
- Seoan mac Pilib succeeds Tomas mor mac Mathghamhna as King of East Breifne, in north-central Ireland.
- The city of Afyonkarahisar (in modern-day western Turkey) is conquered by Sultan Beyazid I, of the Ottoman Empire.
- Louis de Valois is created first Duke of Orléans of the second creation.
- Erfurt University is founded in Erfurt, central Germany.
- Penistone Grammar School, later to be one of the first community comprehensive schools in England, is founded near Barnsley, England.
- In central Persia, the Muzzafarid Empire, led by Shah Mansur, rebels against their Timurid occupiers. The rebellion is squashed and the Muzaffarid nobility are executed, ending the Muzaffarid Dynasty in Persia.
- George VII succeeds his popular father, Bagrat V, as King of Georgia.
- Abdul Aziz II becomes Sultan of the Marinid Dynasty in present-day Morocco, after the death of Sultan Abu Al-Abbas.
- Raimondo Del Balzo Orsini succeeds Otto, Duke of Brunswick-Grubenhagen, as Prince of Taranto (now south-eastern Italy).
- Samsenethai succeeds his father, Fa Ngum, as King of Lan Xang (now Laos).
- King James I of Cyprus inherits the title of King of Armenia, after the death of his distant cousin Leo VI (although the Mamluk conquerors from Egypt remain the true rulers).
- A Ming dynasty Chinese record states that 720,000 sheets of toilet paper (two by three ft. in size) alone have been produced for the various members of the imperial court at Beijing, while the Imperial Bureau of Supplies also reports that 15,000 sheets of toilet paper alone have been designated for the royal family (made of fine soft yellow tissue and perfumed).
- Bosnia resists an invasion by the Ottoman Empire.
- The Ottoman Turks capture Turnovgrad (now Veliko Tarnovo), the capital city of east Bulgaria. Emperor Ivan Shishman is allowed to remain as puppet ruler of east Bulgaria.
- Despite his treaty with the king of Poland, Roman I of Moldavia supports Fyodor Koriatovych against the king. Losing the battle, he will also lose the throne of Moldavia the next year.
- Sikander Shah I succeeds Muhammad Shah III, as Sultan of Delhi. Sikander Shah I is succeeded two months later by Mahmud II.
- Abu Thabid II succeeds Abu Tashufin II, as ruler of the Abdalwadid Dynasty in present-day eastern Algeria. Abu Thabid is succeeded in the same year by his brother, Abul Hadjdjadj I.
- Konrad von Jungingen succeeds Konrad von Wallenrode, as Grand Master of the Teutonic Knights.
- Maelruanaidh MacDermot succeeds Aedh MacDermot, as King of Magh Luirg in north-central Ireland.
- King Stjepan Dabiša of Bosnia signs the Contract of Djakovice, establishing peace with King Sigismund of Hungary.
- Byzantium loses Thessaly to the growing Ottoman Empire.
- The Ottomans conquer Thessaly (now eastern Greece) and begin an eight-year siege of Constantinople, in the Byzantine Empire. In the same year, they begin building the Anadoluhisarı fortress to defend themselves during the siege.
- Ashikaga Yoshimitsu retires as shōgun of Japan, and is succeeded by his son, Ashikaga Yoshimochi.
- Gyeongbokgung Palace and the Jongmyo royal ancestral shrine are built in Hanseong (now Seoul).
- After the death of Sultan Mahmud II, civil war breaks out in the Delhi Sultanate, splitting the state between east and west.
- Battle of Ros-Mhic-Thriúin: The Kingdom of Leinster, led by King Art mac Art MacMurrough-Kavanagh, defeats an invading army from England, led by King Richard II of England and Roger Mortimer, 4th Earl of March.
- Ştefan I succeeds Roman I, as Prince of Moldavia (now Moldova and eastern Romania).
- Abu Zayyan II succeeds his brother, Abul Hadjdjadj I, as ruler of the Abdalwadid Dynasty in present-day eastern Algeria.
- Abd al-Aziz II succeeds Abu al-Abbas Ahmad II, as ruler of the Hafsid Dynasty in present-day Tunisia.
- The Allgäuer Brauhaus brewery is founded in present-day Germany.
- The Hongwu Emperor of the Ming dynasty in China orders the Ministry of Public Works to issue a public notice, that every 100 households in the lijia system are to set aside 2 mu (1,390 m2) of land, for planting mulberry and jujube trees.
- February 12 – The army led by Sigismund of Luxembourg is ambushed by Stephen I of Moldavia, on its way back after conquering Neamț Citadel, and the Hungarians must retreat empty handed.
- April 15 – Tokhtamysh–Timur war – Battle of the Terek River: Timur defeats Tokhtamysh of the Golden Horde at the Volga. The Golden Horde capital city, Sarai, is razed to the ground, and Timur installs a puppet ruler on the Golden Horde throne. Tokhtamysh escapes to Lithuania.
- May 1 – The Duchy of Milan is created, after Lord Gian Galeazzo Visconti of Milan buys the title of Duke from Wenceslaus, King of the Romans.
- May 17
- June 3 – Sultan Bayezid I of the Ottoman Empire beheads Emperor Ivan Shishman of Ottoman-occupied eastern Bulgaria, after Shishman is accused of collaborating with the Wallachians during the 1394 Battle of Karanovasa.
- August 29 – Albert IV succeeds his father, Albert III, as Duke of Austria.
- September 8 – The death of King Stjepan Dabiša leads to the election of his wife Jelena Gruba as Queen of Bosnia. However, most of the Bosnian land is soon appropriated by King Sigismund of [[H
- May 19 – Martin I succeeds his brother, John I, as King of Aragon (modern-day north-east Spain).
- July 20 – Queen Margaret I of Denmark, Norway and Sweden publishes the Treaty of Kalmar, proposing the personal union of the three kingdoms of Denmark, Norway (with Iceland, Greenland, the Faroe Islands, Shetland and Orkney) and Sweden (including Finland and the Åland Islands).
- July 23 – Queen Margaret makes her great-nephew and adopted son Eric of Pomerania joint ruler of Sweden. Eric has already been made joint ruler of Norway.
- September – Battle of the North Inch ("Battle of the Thirty"): In a mass trial by combat on the North Inch of Perth, Scotland, the Clan Cameron defeat the Clan Mackintosh.
- September 25 – Battle of Nicopolis: The Ottomans defeat a joint crusade by Hungary, France, the Holy Roman Empire, England and Wallachia, led by King Sigismund of Hungary. This is the last large-scale crusade of the Middle Ages.
- October – A Transylvanian expedition captures Vlad I Uzurpatorul, thus allowing the restoration of Mircea I of Wallachia to the throne.
- October 31 – The widowed Richard II of England (29), and six-year-old Isabella of Valois (daughter of Charles VI of France), are married in Calais, resulting in a temporary peace between the kingdoms of England and France.
- November 24 – The Transit of Venus, the last not to be part of a pair, is possibly observed by Aztec astronomers.
- November 29 – Ralph Neville, 1st Earl of Westmorland, marries Joan Beaufort in England.
- The Ottomans capture the Bulgarian fortress of Vidin and Tsar Ivan Sratsimir, ending the Second Bulgarian Empire. The Bulgarian state is reestablished in 1878 as the Principality of Bulgaria.
- France conquers the Republic of Genoa.
- After a 14-year interregnum, Pedro de San Superano is declared ruler of the Principality of Achaea (modern-day Peloponnese, southern Greece).
- Abu Amir succeeds Abdul Aziz II as ruler of the Marinid dynasty, in modern-day Morocco.
- Timur appoints his son Miran Shah, as Timurid viceroy of present-day Azerbaijan.
- The Kart dynasty is brought to an end in east Persia after its remaining rulers are murdered at a banquet by Miran Shah.
- Philibert de Naillac succeeds Juan Fernández de Heredia, as Grand Master of the Knights Hospitaller.
- Huitzilihuitl succeeds his father, Acamapichtli, as ruler of the Aztecs.
- The Ulu Camii Mosque is built in Bursa by the Ottomans.
- The Ming dynasty court of China sends two envoys, Qian Guxun and Li Sicong, to the Ava Kingdom of Burma and the Tai polity of the Mong Mao, in order to resolve a dispute between these two. The travels of the Chinese ambassadors are recorded in the historical text of the Baiyi Zhuan.
- Timur orders the construction of a garden in a meadow, House of Flowers.
- Peasants in the modern-day provinces of Hunan and Hupeh in the east of China plant 84 million fruit trees.
- The University of Zadar is founded, the first university in Croatia.
- The Ottomans capture's the town of Vidin, the capital of the Tsardom of Vidin, the only remaining independent Bulgarian state. Emperor Ivan Sratsimir of Vidin is taken prisoner by early this year and later disappears while his son Constantine II becomes Emperor in his place.
- Temür Qutlugh is crowned as the Khan of Golden Horde with the help of general Edigu, although Edigu continues to hold the real power.
- The Università, a form of local government, is established in Malta.
- The Kirillo-Belozersky Monastery is founded in north-west Russia.
- The Sretensky Monastery is founded in Moscow.
- The first hospital in al-Andalus is created, at Granada.
- Neuhausergasse 4, the brewer of Spaten, is listed on the register of Munich breweries.
- Gregory of Tatev writes the Book of Questions, a ten-volume encyclopedic work, at the Tatev Monastery, in Armenia.
- March 15 – Trần Thuận Tông is forced to abdicate as ruler of the Trần dynasty in modern-day Vietnam in favour of his three-year-old son Trần Thiếu Đế.
- April/May – The Bosnian nobility dethrone Queen Helen and replace her with Stephen Ostoja.
- June 25 – Jianwen succeeds his grandfather, Hongwu, as Emperor of Ming dynasty China.
- July – The Stecknitz Canal is completed between the rivers Elbe and Trave (at Lübeck) in modern-day north Germany, one of the earliest navigable summit level canals in the world.
- October 12 – The Treaty of Salynas is signed by Vytautas, Grand Duke of Lithuania, and Konrad von Jungingen, Grand Master of the Teutonic Knights, in an attempt to cede Samogitia to the Knights.
- October 14 – King Taejo of Joseon abdicates the throne of the Joseon dynasty in modern-day Korea following the murder of his heir Yi Bangsuk during a coup by Yi's older half-brother, Yi Bang-won. Taejo's eldest son Jeongjong succeeds to the throne.
- November 11 – Janus succeeds his father, James I, as King of Cyprus and claimant to the throne of Armenian Cilicia.
- December 17 – Timur defeats the last ruler of the Delhi Sultanate, which has been weakened after four years of civil war. Following his victory, Timur's Islamic troops sack the city of Delhi, and proceed to massacre hundreds of thousands of the state's Hindu inhabitants.
- The Teutonic Knights recommence their raids of Lithuania.
- The Teutonic Knights conquer the island of Gotland, near Sweden, which has previously been run by the piratical Victual Brothers.
- Martin of Aragon launches a crusade against the Moors in North Africa.
- The Kingdom of Singapura falls, after being invaded by the Majapahit Empire.
- Abdullah succeeds Abu Amir as ruler of the Marinid dynasty in modern-day Morocco.
- Bunei succeeds his father, Satto, as King of Chūzan (modern-day central Okinawa, Japan).
- Glendalough monastery in Wicklow, Ireland is destroyed by English troops.
- Ferapontov Monastery is founded in modern-day north-west Russia by Therapont of Belozersk.
- The Munmyo Confucian shrine and Sungkyunkwan University are founded in modern-day Seoul.
- Mount Grace Priory is established in Yorkshire, England.
- According to fringe theorists, the Scottish explorer Henry I Sinclair, Earl of Orkney, reaches North America.
- January – Timur the Lame captures and sacks Haridwar.
- February 3 – John of Gaunt, uncle of King Richard II of England and father of Henry Bolingbroke, dies.
- March 18 – Richard II of England cancels the legal documents allowing the exiled Henry Bolingbroke to inherit his father's lands.
- July 4 – While Richard II of England is away on a military campaign in Ireland, Henry Bolingbroke, with exiled former Archbishop of Canterbury Thomas Arundel as an advisor, returns to England and begins a military campaign to reclaim his confiscated lands.
- August 6 – Prince of Yan (Zhu Di) of China starts a rebellion in Beijing.
- August 12 – Battle of the Vorskla River: Mongol Golden Horde forces, led by Khan Temür Qutlugh and Emir Edigu, annihilate a crusading army led by former Golden Horde Khan Tokhtamysh, and Grand Duke Vytautas of Lithuania.
- August 19 – Richard II of England is taken prisoner upon his return from Ireland.
- September 29 – Having regained his father's lands, Henry Bolingbroke is urged to take the crown from the unpopular Richard II of England. Parliament charges Richard II with committing crimes against his subjects and eventually forces him to abdicate.
- September 30 – Parliament accepts Henry Bolingbroke as the new king of England.
- October 13 – Henry IV of England is crowned.
- October 19 – Thomas Arundel is restored as Archbishop of Canterbury, replacing Roger Walden.
- November 1 – John V, Duke of Brittany begins his reign.
Information as of:
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