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1368 – Armies of Olgerd, Grand Prince of Russia, Lithuania and Zhemaitia, and Mikhail Aleksandrovich, Grand Prince of Tver, captured Moscow. Serpukhov goes to Lithuania. Mikhail
Aleksandrovich became Grand Prince of Vladimir – official head of North-East Russia.
1372 – Olgerd completely eliminate the independence of Moscow. House of Kalita overthrown. Dmitry Mikhailovich Bobrok (Olgerd’s nephew) became new prince of Moscow.
1377 – Olgerd’s death. Jagiello, his eldest son by his second wife became new Grand Prince. Against him rebels Olgerd’s brother Keistut of Lithuania and Olgerd’s sons by first wife
Vingald (Andrew) of Polotsk and Dmitry of Bryansk. Usobitsa (dynastic war) starts.
1385-1386 – Jagiello, Grand Prince of Russia, Lithuania and Zhemaitia became King of Poland (as Vladislav II) and moved to Catholicism, which caused dissatisfaction among the Orthodox Russian nobility.
1386-1392 – new usobitsa between Jagiello (Vladislav) and Keistut ‘s son Witovt (Alexander).
1392 - war ends split the territories – Jagiello became polish king, and Witovt (Alexander) – Lithuanian Grand Prince.
1401 – Witovt makes the Novgorod republic to recognize him as “gosudar” (protector).
1407 - under the pretext of protection of the Teutonic Knights, Witovt subjugates Pskov
1408-1410 – Witovt conquers Beloozero, Ustyug and Vologda
1421 – Ryazan became Lithuanian vassal.
1427 - Witovt crown’s in Lutsk as king of Russia and Lithuania
1430 – after Witovt’s death, his brother Sigismund (Catholic) crowned as new king.
1432 – palace coup in Vilna. Unpopular Sigismund is killed. Olelko Vladimirovich, prince of Kiev and Olderd’s grandson became the new king (As Alexander II). During his regin Orthodoxy is the main religion of Russia.
To 1460 –Nizhni Novgorod – the last adversary of the Lithuanian kings in North-East Russia falls.
1475 – Russian troops help Italian city-states of Tana (OTL Azov), Kafa (OTL Feodosia) and Soldaia (OTL Sudak) to beat off Ottoman attack.
To 1480 – “Jewish heresy” starts in Russia – antitrinitarist doctrine, which come out to cheap church. Started in Novgorod, it soon enjoy popularity not only in low classes, but partly in nobility and even among some members of Olelkovich dynasty.
1477 – Novgorod became part of the Kingdom of Russia and Lithuania as an autonomous principality.
1492 – Vladislav II of Hungary and IV of Bohemia elected new Polish king.
1497 – Polish plan to make prince Sigismund gospodar of Moldavia falls.
1505 – last Grand Prince of Tver and Vladimir, Mihail III, dies without heir. So, territory of the principaty goes to Russia.
1509-1511 – Ottoman-Polish war in Moldavia.
1526-1531 – Crimean War. Ottoman armies takes Russian cities in Crimea – Kafa(OTL Feodosia), Soldaia (OTL Sudak), Korchev (OTL Kerch), Chersoneses (OTL Sevastopol) and Solhat (near OTL Simferopol). Perecop isthmus became new Russian-Ottoman border.
1533 – Ottomans attack Hungary. King Louis II is defeated and die in battle near Temeshvar. His son and heir, Istvan VI is only 5-years old, so his uncle and Polish king Sigismund proclaimed as regent.
1535 – Istvan VI of Hungary and Bohemia died (m.b. poisoned). His uncle and Regent, Polish King Sigismund I is elected a new king (as Sigismund II). It caused a war with Austria.
1537 – Ottomans captures Vienna. Eastern Habsburg’s capital moved to Ghent.
1554 – Holy Roman Emperor Charles V divided Habsburg Empire among the successors. His brother Ferdinand received the title of Holy Roman Emperor and possessions inside the Empire, son Philip – all territories outside the Germany – Spain, Naples and Americas.
1560 – Livonia became a vassal of Russia
1570 – Both Ottoman and Habsburg threats unites the Union of Poland, Bohemia and Hungary, and on the king Sigismund-August initiative the new nation was born – Republic of Three Nations, joined together “as equal with equal, free with the free, noble with noble”.
1572 – death of Sigismund-August , Henry of Valois, brother of the French king was elected as the new king of RTN.
1576 – with the French support, Henry of Valois was elected Holy Roman Emperor (as Henry VIII). the prospect of unification of France and Germany could not be good for Spain, so German War start.
1586 – Yuri III, the last king of Russia from Olelkowicz’s dynasty dies, leaving no male heir. His only daughter, Sofia, was only 5 year old, so nobility and clergy elected crown Hetman and Protestant Mikalaj (Nicolas) Radzivil new king. During his reign, Russian cities were granted the Magdeburg Law. Also, he improved relations with the Protestant countries and refocused foreign policy from the Empire to principalities of the Evangelical Union and Denmark. Union with Denmark was sealed with the dynastic marriage of Hans Oldenburg and Halashka Radzivil in 1599.
1592 – nobleman and Samogitian Starasta (Marshal of the Nobility) Ivan Chadkievič rebelled against King Mikalaj. The uprising was crushed.
1598 – After the death of the Henry of Valois, Mikalaj Radzivil was elected king of RTN (as Nicholas I).
1599 – civil war starts in Sweden between the Catholic king Johan IV and Protestant Karl Duke of Östergötland.