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By the middle of the 14th c. there were three principalities within Bulgarian territories - the Turnovo, the Vidin and the Dobrudzha Principality. The German historian Hans Schilberger called them "the three Bulgarias". Divided, Bulgaria was an easy prey for the Ottoman Turks, who set foot permanently on the European continent for the first time in 1352. They conquered Borui (today's Stara Zagora) and Plovdiv and made the Ederne fortress their capital.

On 26 September 1371 a large Christian army, led by the Macedonian rulers, the brothers Vulkashin and John Uglesha, met the Turks in a bloody battle at Chernomen (near today's Svilengrad). They were defeated and the Turks headed for the heart of Bulgarian territories.

The young Bulgarian King Ivan Shishman (1371 - 1395) acknowledged himself as Turkish vassal, agreed to take part in the military operations of the Sultan and to pay him yearly tax. In 1385 - 1386 Sofia, Pirot and Nish, Provadia, Shoumen and Silistra were conquered one after the other. Although Sultan Murad I was killed in the battle of Kossovo pole (1389), the Ottoman army won a victory over the Serbs. Now it was the turn of the Turnovo kingdom. After a three-month siege, on 17 July 1393 the Turnovo fortress was conquered. King Ivan Shishman found refuge in the Nikopol fortress where he was captured and slain (3 June 1395). The same year the Dobrudzha Principality was also conquered.

An island in the sea of subjugated territories, the Vidin Principality was subjected to Sultan Bayazid I in 1396 and its ruler Ivan Sratsimir was taken to Ottoman territories in Asia Minor.

In this way, one after the other, Bulgarian kingdoms and principalities disappeared from the map of Europe. In the following 500 years the Bulgarian people suffered one of the most trying periods in their history.

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