Battle of Chernomen and its consequences
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Was a battle between the Ottoman Empire and the Serbian Empire that lead to the loss of southern Serbia to the Ottomans.
Chronology
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January 1374: In 1373 Ivan Shishman, the ruler of Moravian Serbia, was forced to negotiate a humiliating peace treaty: he became an Ottoman vassal strengthening the union with a marriage between Murad and Shishman's sister Kera Tamara. To compensate, the Ottomans returned some of the conquered lands, including Ihtiman and Samokov.
October 1371: In 1371, the Ottoman Beylik captured the territory of Sozopol, a historic town on the Black Sea coast of Bulgaria.
November 1371: The Ottomans succeeded capturing the cities of Drama, Kavála, and Serrai in modern Greece.
November 1371: Immediately after the battle of Chernomen, the armies of Murad I embarked on another campaign overrunning Northern Thrace and forcing Ivan Shishman of Bulgaria to pull back north of the Balkan Mountains.
November 1371: In 1371, during the Ottoman conquest of the Balkans, one of Ivan Shishman's voivodes, Shishkin, was killed in battle in the Rhodopes region. This event further facilitated the Ottoman Beylik's control over Kostenets, Ihtiman, and Samokov.
November 1371: In 1371, the Ottoman Beylik, led by Murad I, captured Bitola in the southwest after a bloody siege.
November 1371: The Ottomasn conquered the whole bulgarian state with the exception of lands to the north of the Balkan mountains and the Valley of Sofia.
January 1374: Between 1371 and 1373 the Ottomans emerged as a considerable power on the Balkans. They ruled over the entire Thrace and had seized the lands of Uglesha in Eastern Macedonia.