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Persian Empire
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Kingdom of Paeonia
- 440s BC: The Paeonian tribes coalesce into a kingdom.
- after 400 BC: Agis becomes king of Paeonia.
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- 358 BC: The Hellenistic Macedonia reduces the Paeonian kingdom to a semi-autonomous, subordinate status with as king Lycceius.
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Kingdom of Macedonia
- 336 BC: Paeonia is fully incorporated into Macedonia.
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Roman Republic
- 146 BC: The region is conquered by and annexed to Rome.
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Roman Empire
- 27 BC: Gaius Octavianus becomes sole ruler of Rome and as Augustus the first emperor.
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Byzantine Empire
- 395: With the partition of the Roman Empire, the region becomes part of the (Eastern) Roman Empire, also rendered as Byzantine Empire.
- 580s: Slavs settle in the region.
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Bulgarian Khanate
- 681: Asparuch of the Bulgars defeats the Byzantines. The Byzantine Empire has to accept a Bulgarian state within its territory, including present-day Macedonia. The Bulgars merge with the Thracians, Vlachs and Slavs and are Slavicized.
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Principality of Bulgaria
- 864: Bulgaria is continued as principality.
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Bulgarian Empire
- 913: Bulgaria becomes an empire.
- 971: After a succesful invasion of Thrace and Bulgaria, grand prince Sviatoslav of Rus' is defeated by the Byzantine emperor Ioannis Tzimiskes. After the capture of the Bulgarian tsar Boris II, he claims the annexation of Bulgaria. The conquest of Bulgaria commences.
- 981: Basileios II begins the final conquest of Bulgaria.
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Byzantine Empire
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Bulgarian Empire
- 1185: After a revolt against the Byzantine rulers, Ivan Asen becomes emperor of Bulgaria. The liberation war lasts until 1204.
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Kingdom of Serbia
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Empire of the Serbs and Greeks
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Kingdom of Prilep
- 1371: Serbia is continued in the region by the Kingdom of Prilep, ruled by Marko Mrnjavčević.
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Subleme Ottoman Empire
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Kruševo Republic
- 1903: Kruševo, led by president Nikola Karev, secedes unrecognized from the Ottoman Empire.
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Kingdom of Serbia
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Kingdom of Bulgaria
- 1915: Bulgaria conquers parts of Serbia in World War I.
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Kingdom of Serbs, Croats and Slovenes
- 1918: Bulgaria is defeated by the allied forces. Montenegro joins Serbia and Serbia merges the same year with the State of Slovenes, Croats and Serbs into the Kingdom of Serbs, Croats and Slovenes, a.k.a Yugoslavia.
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Kingdom of Yugoslavia
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Kingdom of Bulgaria
- 1941: Most of Vardar Banovina is annexed to Bulgaria.
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Albanian Kingdom
- 1941: Part of Vardar Banovina is annexed to Italian Albania.
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- 1943: Albania becomes a German puppet state.
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Kingdom of Yugoslavia
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Federal People's Republic of Yugoslavia
- 1945: A new of government of Yugoslavia is formed by Tito. The National Liberation Army defeats Croatia, the Slovenian Home Guard and the remaining German forces and liberates Yugoslavia. Yugoslavia is restored. The People's Republic of Macedonia is established as one of the members of the federation.
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Socialist Federal Republic of Yugoslavia
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Republic of Macedonia
- 1991: After the electorate supports in a referendum independence, Macedonia secedes as a democratic republic from Yugoslavia, recognized in 1993. Due to the position of Greece often recognized as the Former Yugoslav Republic of Macedonia.
- 1992. A new constitution stipulates that Macedonia has a parliament elected in free multi-party elections and a popularly elected president. The government is responsible to the parliament.
- 1993: Macedonia joins the United Nations.
- 1995: Macedonia joins the Council of Europe.
- 2001: During the insurgencies the National Liberation Army of Albanians in Macedonia is active against the state. After the Ohrid Agreement that ends the insurgencies it is disarmed. The Albanian National Army continues as an terrorist movement.
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