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|Centuries:||13th century – 14th century – 15th century|
|Decades:||1360s 1370s 1380s – 1390s – 1400s 1410s 1420s|
|Years:||1396 1397 1398 – 1399 – 1400 1401 1402|
|1399 by topic|
|State leaders - Sovereign states|
|Birth and death categories|
|Births - Deaths|
|Establishments and disestablishments categories|
|Establishments - Disestablishments|
|Art and literature|
|1399 in poetry|
|Ab urbe condita||2152|
|Bahá'í calendar||-445 – -444|
|English Regnal year||22 Ric. 2 – 1 Hen. 4|
|Chinese calendar||戊寅年 (Earth Tiger)
4095 or 4035
— to —
己卯年 (Earth Rabbit)
4096 or 4036
|- Vikram Samvat||1455–1456|
|- Shaka Samvat||1321–1322|
|- Kali Yuga||4500–4501|
|Japanese calendar||Ōei 6
|Minguo calendar||513 before ROC
|Thai solar calendar||1942|
|Wikimedia Commons has media related to 1399.|
- 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.
- Richard II cancels the legal documents allowing the exiled Henry Bolingbroke to inherit his father's land.
- While Richard II 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 land.
- After regaining his power, Henry Bolingbroke is urged to take the crown from the unpopular Richard II. Richard is taken prisoner upon his returns from Ireland and eventually forced to abdicate. Parliament then charges Richard with committing crimes against his subjects.
- August 6 – Prince of Yan(Zhu Di) of China started rebellion in Beijing
- August 12 – Battle of the Vorskla River: Mongol Golden Horde forces led by Khan Temur Qutlugh and emir Edigu annihilate a crusading army led by former Golden Horde Khan Tokhtamysh and Grand Duke Vytautas of Lithuania.
- 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 VI, Duke of Brittany begins his reign.
- Faraj succeeds his father, Barquq, as Mamluk Sultan of Egypt.
- Sultan Bayezid I of the Ottoman Empire invades Mamluk-occupied Syria. A rift forms between Sultan Bayezid and Timur of the Timurid Empire, who also wanted to conquer Syria.
- Ladislaus regains the throne of Naples after overthrowing King Louis II.
- King Jogaila becomes sole ruler of Poland after the death of his co-ruling wife, Queen Jadwiga.
- Abu Said Uthman III succeeds Abdullah as ruler of the Marinid dynasty in present-day Morocco.
- The Principality of Achaea (now southern Greece) resists an invasion by the Ottoman Empire.
- date unknown
- January 4 – Nicolau Aymerich, Catalan theologian and inquisitor
- February 3 – John of Gaunt, 1st Duke of Lancaster (b. 1340)
- May 12 – Demetrius I Starszy, Prince of Trubczewsk (in battle) (b. 1327)
- July 13 – Peter Parler, German architect (b. 1330)
- July 17 – Queen Jadwiga, joint ruler of Poland
- September 22 – Thomas de Mowbray, 1st Duke of Norfolk, English politician (b. 1366)
- November 1 – John V, Duke of Brittany (b. 1339)
- date unknown