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|Ab urbe condita||2252|
|Balinese saka calendar||1420–1421|
|English Regnal year||14 Hen. 7 – 15 Hen. 7|
|Chinese calendar||戊午年 (Earth Horse)|
4195 or 4135
— to —
己未年 (Earth Goat)
4196 or 4136
|- Vikram Samvat||1555–1556|
|- Shaka Samvat||1420–1421|
|- Kali Yuga||4599–4600|
|Japanese calendar||Meiō 8|
|Minguo calendar||413 before ROC|
|Thai solar calendar||2041–2042|
1625 or 1244 or 472
— to —
1626 or 1245 or 473
|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.
- May 19 – 13-year-old Catherine of Aragon, the future first wife of Henry VIII of England, is married by proxy to his brother, 12-year-old Arthur, Prince of Wales.
- 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, by Alonso de Ojeda and Amerigo Vespucci.
- 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 Tréguier (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 Plantagenet, 17th Earl of Warwick, last male member of the House of York, is executed for reportedly attempting to escape from the Tower of London.
- December 18 – The Rebellion of the Alpujarras (1499–1501) begins in the Kingdom of Granada (Crown of Castile).
- 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 is writing on steganography.
- Heinrich Cornelius Agrippa matriculates at Cologne University.
- Giggleswick School is founded by Reverend James Carr, in England.
- January 15 – Samuel Maciejowski, Polish bishop (d. 1550)
- January 20 – Sebastian Franck, German humanist (d. 1543)
- January 29 – Katharina von Bora, German nun, wife of Martin Luther (d. 1552)
- February 10 – Thomas Platter, Swiss humanist scholar and writer (d. 1582)
- March 22 – Johann Carion, German astrologer and chronicler (d. 1537)
- March 31 – Pope Pius IV (d. 1565)
- May 14 – Agostino Gallo, Italian agronomist (d. 1570)
- June 24 – Johannes Brenz, German theologian and Protestant Reformer of the Duchy of Württemberg (d. 1570)
- July 17 – Maria Salviati, Italian noble and mother of Cosimo I de Medici (d. 1543)
- August 14 – John de Vere, 14th Earl of Oxford, English noble (d. 1526)
- September 3 – Diane de Poitiers, French duchess, mistress of Henry II of France (d. 1566)
- October 13 – Claude of France, queen consort of France, daughter of Louis XII of France (d. 1524)
- October 14 – Catherine of the Palatinate, Abbess of Neuburg am Neckar (d. 1526)
- October 31 – Günther XL, Count of Schwarzburg (1526–1552) (d. 1552)
- November 1 – Rodrigo of Aragon, Italian noble (d. 1512)
- December 8 – Sebald Heyden, German musicologist and theologian (d. 1561)
- December 13 – Justus Menius, German Lutheran pastor (d. 1558)
- 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)
- Niccolò Fontana Tartaglia, Italian mathematician (d. 1557)
- Ming, Icelandic clam (d. 2006)
- probable – Juan Rodríguez Cabrillo, Portuguese explorer (d. 1543)
- January 9 – John Cicero, Elector of Brandenburg (b. 1455)
- March 24 – Edward Stafford, 2nd Earl of Wiltshire, English nobleman (b. 1470)
- April 7 – Galeotto I Pico, Duke of Mirandola (b. 1442)
- August 29 – Alesso 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 Plantagenet, 17th Earl of Warwick, last male member of the English House of York (b. 1475)
- date unknown