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| 1394 |
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| The Ottomans conquered Thessaly and imposed a blockade on Constantinople that lasted until 1402. | 1 |
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| 1395 |
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| The Ottomans occupied the Dobruja and invaded Wallachia and Hungary. | 2 |
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| 1396 |
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| The Crusade of Nicopolis. A large allied army drawn from many countries in Europe and led by King Sigismund of Hungary advanced against the Ottomans, along the Danube. The Ottomans defeated these Crusaders near Nicopolis (Sept. 25) in a major victory that consolidated their hold in the Balkans (See 1396). | 3 |
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| 1397–99 |
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| Ottoman occupation of Karaman (1397), the state of Kadi Burhaneddin based in Sivas (1398), and the areas of Elbistan and Malatya west of the Euphrates (1399); Ottoman control was thus extended over most of Anatolia. | 4 |
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