Spain

• 1469: The Union of the Catholic Monarchs, Isabella I of Castille and Ferdinand II of Aragon, Spain is founded by the union of the Crown of Aragon and the Crown of Castille (Display only Castile, Aragon shall not be included until 1479). Flag: (http://www.tzorafolk.com/genealogy/history/arms/catholic-kings-(1492-1506).png)
• 1475: Spanish flag is now this one (https://en.wikipedia.org/wiki/File:Pend%C3%B3n_her%C3%A1ldico_de_los_Reyes_Catolicos_de_1475-1492.svg)
• 1476: Temporal occuppation of Cape Verde and occuppation of Santa Cruz de la Mar Pequeña
• 1478: Battle of Guinea between Castille and Portugal
• 1479: Ferdinand II is now in the throne of Aragon, thus officially beginning the personal union between Castile and Aragon 
• 1480: Ottomans ocuppy Otranto
• 1481: Otranto liberated by Spanish troops
• 1482: Conquest of Gran Canaria and beginning of the Grenada War
• 1485: Castilian troops ocuppy Ronda and Marbella from Grenada 
• 1487: Castilian troops ocuppy Malaga
• 1488: Castilian troops ocuppy Vera
• 1489: Castilian troops ocuppy Baza and Almería
• 1490: The city of Granada is surrounded
• 1492: Granada is conquered
• 1492: Conquest of La Palma
• 1492: 12 October: Columbus discovers the New World, the Bahamas are conqured
• 1492: The colony of La Navidad founded in the north of Haiti
• March 1494: The colony of La Isabela founded in the north of Dominican Republic
• 1495: Conquest of Tenerife
• 1495: Naples falls to French ocuppation
• 1496: The colony of Santo Domingo founded
• 1496: France loses Naples
• 1496: Conquest of the Hispaniola
• 1497: Conquest of Melilla
• 1501: Parts of Naples ocuppied, from Salerno to Apulia
• 1503: Spain ocuppies the city of Naples
• 1504: Naples is totally conquered and annexed to the crown
• 1504: Isabel of Castile dies, leaving the throne to Ferdinand of Aragon
• 1505: Annexion of Bermuda. Conquest of Mazalquivir
• 1508: Conquest of Puerto Rico and Oran
• 1509: Conquest of Jamaica
• 1510: Spain conquers Algiers and Bujia
• 1510: Conquest of a part of Panama
• 1511: Conquest of Cuba, the Cayman Islands and Tripoli (modern capital of Libya)
• 1511: Part of Puerto Rico rebels
• 1512: Cispyrenaical Navarre is annexes into Castile
• 1513: The colony of Castilla de Oro is founded in Panama
• 1513: Puerto Rico surrenders
• 1516: Ferdinand II dies. Charles I is in the throne of Spain. Spain is de facto a country. Flag: (https://en.wikipedia.org/wiki/File:Flag_of_Cross_of_Burgundy.svg)
• 1516: Conquest of Algiers
• 1517: Conquest of Tlemcen
• 1519: Spain begins it's campaign against the Aztec empire
• 1520: Conquest of Tlaxcala
• 1520: Castilla de Oro colony expands
• 13 August 1521: The Aztec Empire is totally conquered and annexed
• 1521: Marianas islands and Guam discovered
• 1521: Spain ocuppies Milan
• 1522: Spain ocuppies Genoa
• 1522: Annexion of most of Central America and conquest of Michoacan
• 1522: Spain abandons Tripoli
• 1523: Spain conquers Chiapas
• 1524: Spain ocuppies part of Provence, Nize and Touloun
• 1524: Spain conquers Guatemala
• 1525: Spain leaves European conquests but Naples
• 1525: Spain gives Santa Cruz de la Mar Pequeña to Morocco
• 1526: Spain occuppies Milan
• 1527: Annexion of a part of Yucatan
• 1527: France lands around Naples and lays siege to the city
• 1528: Spain annexes Chiapas
• 1529: Spain leaves Milan
• 1529: France leaves Naples. Spain besieges Florence
• 1529: Annexion of the Marshall Islands
• 1530: Annexion of more of Yucatan
• 1530: Spain abandons Italy but Naples and Milan
• 1530: Spain releases Malta
• 1531: Begining of the conquest of the Inca Empire with a landing in Ecuador
• 1533: The Inca Empire is conquered, the colony of New Castille founded. Cañari is also conquered. Keep advancing down into Chile until 1537
• 1535: Spain annexes Milan
• 1535: Spain conquers the city of Tunis
• 1535: Conquest of a part of Mexican Pacific coast and part of Colombian Atlantic coast. Viceroyalty of New Spain formed
• 1536: Conquest of Rio de la Plata and ocuppation of parts of Provence
• 1537: Conquest of Chile
• 1537: Spain abandons Provence
• 1537: First Jesuite mission to Paraguay
• 1538: Conquest of a part of Bolivia
• 1539: Expansion in New Grenada
• 1540: Expansion in Chile
• 1540: Spain conquers part of Central Mexico
• 1541: Rio de la Plata lost
• 1541: Spain claims the Mississipi river and all of their afluents. Another expedition reaches Lindsborg, Kansas, losing it next year. Captaincy General of Chile founded
• 1542: Viceroyalty of Peru founded
• 1542: More of Central Mexico is conquered
• 1543: Spain ocuppies part of Provence and Savoy
• 1544: Slow retrocession in France
• 1546: Spain leaves Savoy 
• 1550: Spain conquers Mahdia, Tunisia
• 1553: Spain leaves Mahdia
• 1553: Conquest of a part of the Chaco plains
• 1555: Spain annexes Ebla and Piombino
• 1556: Spain inherits the French Comte and the Low Countries after Charles I abdicated. Spain is now ruled by Philip II.
• 1557: Spain inherits some areas in Tuscany
• 1560: Connexion between the Jesuite Mission and Peru Viceroyalty
• 1560: Conquest of more of the Chaco
• 1564: Annexion of Guam
• 1565: Annexion of the Marianas islands and discovery of the Philippines
• 1565: Colony of Florida founded
• 1565: Discovery of the Californian channel islands
• 1566: Exapnsion of Florida
• 1570: Expansion in Mexico
• 1571: Expansion in the Philippines
• 1572: The Dutch rebel against Spain
• 1573: Expansion in Argentina
• 1573: Expansion in the Philippines
• 1574: Discovery of Palau
• 1574: Spain leaves Tunis
• 1579: The Dutch advance more
• 1579: Expansion in the Philippines
• 1580: Rio de la Plata is recaptured
• 1580: Spain inherits Portugal except for the Azores
• 1580: The Dutch rebels have control of much of the Low Countries
• 1583: Spain conquers the Azores
• 1584: Spain recaputres some land from the Netherlands
• 1585: Expansion in the Philippines
• 1586: Colony of Angola founded
• 1589: Spain conquers Tondo
• 1591: The Netherlands captures some more land
• 1598: Philip II dies, Philip III begins to rule 
• 1598: Spain conquers the southern shore of the Rio Grande
• 1602: Bahrain is abandoned
• 1605: El Paso founded
• 1609: Britain captures Bermuda
• 1609: Expansion in the Philippines
• 1610: Spain expands up the Rio Grande into New Mexico
• 1613: Expansion of Florida
• 1615: Expansion of Brazil
• 1615: Bandar Abbas ceded to Persia
• 1617: Another expansion of Brazil
• 1621: Philip III dies leaving the throne to Philip IV
• 1624: Expansion in Ceylan
• 1626: Spain captures a small part of the Netherlands
• 1626: Annexion of northern Taiwan
• 1629: Netherlands capture a small part of the Spanish Flandes. Spain conquers Saint Kitts and Nevis
• 1630: The Netherlands take Recife. Spain abandons Saint Kitts and Nevis
• 1630: Expansion in Colombia
• 1633: Expansion in Mexico
• 1636: Expansion in the Philippines
• 1637: Another small dutch capture of land in Spanish Flandes
• 1638: Conquest of a part of the Amazonas
• 1640: Portugal secedes
• 1640: Catalan revolt begins
• 1642: Taiwan is abandoned
• 1645: The Netherlands make a small advance in the other side of the Rhine
• 1645: Expansion of the Philippines
• 1648: The Netherlands and France get a part of the Spanish Flandes
• 1655: Britain captures Jamaica
• 1659: Catalan Revolt ends: Peace of the Pyrenees
• 1665: Philip IV dies leaving the throne to Charles II
• 1668: France gets a small part of the Spanish Flandes
• 1670: Cayman Islands and Jamaica lost
• 1673: Spain leaves it's claims over the Mississipi
• 1679: France annexes the Spanish French Compte
• 1684: Expansion in Bolivia
• 1691: Expansion in Paraguay
• 1697: France takes Haiti
• 1697: Conquest of a part of Baja California
• 1700: Expansion of Florida. Charles II dies leaving the throne to Philip V, but this causes a succession crisis that will turn into a civil war.
• 1701: Flag becomes (https://en.wikipedia.org/wiki/File:Bandera_de_Espa%C3%B1a_1701-1760.svg)
• 1705: Last expansion in the Philippines
• 1706: Milan falls to Austria
• 1712: Spain conquers Chiloé islands
• 1714: The Spanish Flandes is given to Austria
• 1714: Decrees of Nueva Planta: Aragon is destroyed
• 1715: Conquest of the rest of Florida
• 1717: Viceroyalty New Granada proclaimed
• 1718: Expansion in Mexico
• 1718: Britain captures the Bahamas
• 1724: Conquest of Sacramento from Portugal
• 1726: Expansion of Sacramento
• 1736: Expansion in Argentina and Uruguay
• 1746: Ferdinand VI begins to rule
• 1750: Border set with Portugal in America
• 1750: Conquest of the South American cone
• 1759: Charles III begins to rule
• 1760: Flag becomes (https://en.wikipedia.org/wiki/File:Bandera_de_Espa%C3%B1a_1760-1785.svg)
• 1762: Britain ocuppies West Cuba and the city of Manila. Lousiana given from France
• 1763: Sacramento given to Portugal
• 1763: Florida given to Britain
• 1764: Britain abandons Manila
• 1766: Annexion of the Falklands
• 1769: Annexion of the Easter Island
• 1774: Spain colonisies some parts of Polynesia under the name of "Isla de Amat"
• 1776: Viceroyalty of Rio de la Plata
• 1777: Sacramento and parts of Brazil obtained from Portugal
• 1780: Spain occuppies St.Louis on the Mississipi
• 1781: Spain occuppies Florida and West Florida
• 1783: Florida, Minorca and West Florida obtained from Britain
• 1785: Flag becomes (https://en.wikipedia.org/wiki/File:Flag_of_Spain_(1785-1873_and_1875-1931).svg)
• 1788: Charles IV begins to rule
• 1789: Discover of Vancouver Island and reclamation of the Nootka Territory
• 1795: Nootka Territory unclaimed
• 1795: La Hispaniola given to France
• 1797: Spain loses Polynesia
• 1798: Belize given to Britain
• 1800: Louisiana given to France
• 1808: Spain recaptures most of la Hispaniola
• 1808: Ferdinand VII begins to rule 
• 1811: United Provinces of New Granada declares independence
• 1813: Paraguay declares independence
• 1816: Argentina declares independence
• 1816: Spain reconquers Colombia
• 1818: Chile declares independence
• 1819: Colombia declares independence
• 1819: Flordia is given to USA, border adjustement in Mexico
• 1821: Peru declares independence
• 1821: Mexico declares independence
• 1822: Dominican Republic declares independence
• 1822: Ecuador declares independence 
• 1823: French Intervention in Spain
• 1825: Bolivia declares independence
• 1833: Isabel II begins to rule, but the Carlist War begins
• 1839: First Carlist War ends
• 1846: Second Carlist War begins
• 1849: Second Carlist War ends 
• 1851: Spain makes Sulu a vassal state
• 1858: Spain begins a campaign in Cochinchina 
• 1859: Ocuppation of Northern Morocco
• 1860: Acquisition of Sidi Ifni. Northern Morocco abandoned
• 1862: Spain leaves Cochinchina
• 1863: Spain reconquers the Dominican Republic
• 1865: Spain leaves the Dominican Republic
• 1868: Isabel II abdicates and Francisco Serrano is named as regent 
• 1871: Amadeo I begins to rule
• 1873: Amadeo I abdicates and Spain turns into a republic. Flag becomes (https://en.wikipedia.org/wiki/File:Flag_of_the_First_Spanish_Republic.svg)
• 1874: The republic collapses into a kingdom ruled by Alfonso XII. Flag becomes (https://en.wikipedia.org/wiki/File:Flag_of_Spain_(1785-1873_and_1875-1931).svg)
• 1885: Marshall islands given to Germany
• 1886: Alfonso XIII begins to rule
• 1898: American conquest of Puerto Rico, Guam, Cuba and the Philippines. Sulu is abandoned
• 1899: Cession to Germany of Palau, the Carolines and the Marianas islands
• 1912: Morocco is divided between Spain and France. 
• 1920: An insurgency controls most of Spanish Rif, basically this: https://en.wikipedia.org/wiki/File:Rep%C3%BAblica_del_Rif.svg
• 1923: Tangier becomes an international zone
• 1926: The Rif rebellion is supressed.
• 1931: Alfonso XII abdicates and Spain becomes a republic led by Niceto Alcalá-Zamora. Flag becomes (https://en.wikipedia.org/wiki/File:Flag_of_Spain_(1931_-_1939).svg)
• 1936: The civil war begins. Manuel Azaña is president of the republic, and the fascists are led by Francisco Franco. Fascist Flag becomes (https://en.wikipedia.org/wiki/File:Flag_of_Spain_(Civil)_alternate_colours.svg)
• 1938: Fascist Flag becomes (https://en.wikipedia.org/wiki/File:Flag_of_Spain_(1938_-_1945).svg)
• 1939: End of the civil war
• 1940: Spain annexes the international zone of Tangier
• 1945: Spain restores the sovereignity of Tangier. Flag becomes (https://en.wikipedia.org/wiki/File:Flag_of_Spain_(1945_-_1977).svg)
• 1958: Spain cedes Cape Juby to Morocco, and some of Sidi Ifni
• 1975: Juan Carlos I begins to rule in Spain
• 1977: Flag becomes (https://en.wikipedia.org/wiki/File:Flag_of_Spain_(1977_-_1981).svg)
• 1981: Flag becomes (https://en.wikipedia.org/wiki/File:Flag_of_Spain.svg)
• 2014: Philip VI begins to rule