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|Centuries:||14th century – 15th century – 16th century|
|Decades:||1460s 1470s 1480s – 1490s – 1500s 1510s 1520s|
|Years:||1496 1497 1498 – 1499 – 1500 1501 1502|
|1499 by topic|
|Arts and science|
|Architecture - Art|
|State leaders - Sovereign states|
|Birth and death categories|
|Births - Deaths|
|Establishments and disestablishments categories|
|Establishments - Disestablishments|
|Art and literature|
|1499 in poetry|
|Ab urbe condita||2252|
|English Regnal year||14 Hen. 7 – 15 Hen. 7|
— to —己未年十一月廿九日
|- Vikram Samvat||1555–1556|
|- Shaka Samvat||1421–1422|
|- Kali Yuga||4600–4601|
|- Ǹrí Ìgbò||499–500|
|Japanese calendar||Meiō 8
|Juche calendar||N/A (before 1912)|
|Julian calendar||1499 MCDXCIX|
|Minguo calendar||413 before ROC
|Thai solar calendar||2042|
|Wikimedia Commons has media related to: 1499|
- January 8 – Louis XII of France marries Anne of Brittany, in accordance with a law set by his predecessor, Charles VIII.
- April 14 – By the Treaty of Krakow, Poland and Hungary recognize the independence of Moldavia.
- July 22 – Battle of Dornach: The Swiss decisively defeat the army of Maximilian I, Holy Roman Emperor.
- July 28 – First Battle of Lepanto: The Turkish navy wins a decisive victory over the Venetians.
- August – Polydore Vergil completes De inventoribus rerum, the first modern history of inventions.
- August 24 – Lake Maracaibo is discovered.
- September 18 – Vasco da Gama arrives at Lisbon, returning from India, and is received by King Manuel of Portugal.
- September 22 – Treaty of Basel: Maximilian is forced to grant the Swiss de facto independence.
- October 25 – The Pont Notre-Dame in Paris, constructed under Charles VI of France, collapses into the Seine.
- November 5 – The Catholicon is published in Treguier (Brittany). This Breton-French-Latin dictionary had been written in 1464 by Jehan Lagadeuc. It is the first dictionary of either French or Breton.
- November 23 – Perkin Warbeck, pretender to the throne of England, is hanged for reportedly attempting to escape from the Tower of London.
- November 28 – Edward, Earl of Warwick, last male member of the House of York, is executed for reportedly attempting to escape from the Tower of London.
Date unknown 
- The French under Louis XII seize Milan, driving out Duke Ludovico Sforza. Leonardo da Vinci flees to Venice.
- Montenegro, the last free monarchy in the Balkans, is annexed by the Ottoman Empire as part of the sanjak of Shkodër.
- Johannes Trithemius inadvertently reveals interests in magic by writing a letter to a Carmelite monk about a treatise he was writing on steganography.
- Heinrich Cornelius Agrippa matriculates at Cologne University.
- January 20 – Sebastian Franck, German humanist. (d. 1543)
- January 29 – Katharina von Bora, wife of Martin Luther
- February 10 – Thomas Platter, Swiss humanist (d. 1582)
- March 31 – Pope Pius IV (d. 1565)
- September 3 – Diane de Poitiers, mistress of Henry II of France (d. 1566)
- October 13 – Claude of France, queen of Louis XII of France (d. 1524)
- date unknown
- Hans Asper, Swiss painter (d. 1571)
- Michael Coxcie, Flemish painter (d. 1592)
- Cesare Hercolani, Italian military leader (d. 1534)
- Jan Łaski, Polish Protestant reformer (d. 1560)
- Laurentius Petri, Archbishop of Uppsala (d. 1573)
- Giulio Romano, Italian painter (d. 1546)
- Bernardino de Sahagún, Franciscan missionary (d. 1590)
- Niccolo Fontana Tartaglia, Italian mathematician (d. 1557)
- probable – Juan Rodríguez Cabrillo, Portuguese explorer (d. 1543)
- January 9 – John Cicero, Elector of Brandenburg (b. 1455)
- August 29 – Alessio Baldovinetti, Florentine painter (b. 1427)
- October 1 – Marsilio Ficino, Italian philosopher (b. 1433)
- November 23 – Perkin Warbeck, Flemish imposter (b. c. 1474) (executed)
- November 28 – Edward, Earl of Warwick, last male member of the English House of York (b. 1475)
- date unknown